Month: May 2021

Synthetic Route of 13519-90-9, These common heterocyclic compound, 13519-90-9, name is 4-Fluoroisophthalonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

4-hydroxytetrahydropyran (14 g, 140 mmol) was taken up in tetrahydrofuran (300 mL) and cooled in an ice-water bath. Potassium tert-butoxide (17 g, 150 mmol) was added, and the reaction mixture was stirred for 20 minutes in the bath before the addition of 4-fluoroisophthalonitrile (10 g, 68 mmol). The mixture continued to stir in the bath for 5 minutes before the removal of the bath. The mixture was stirred at room temperature overnight and then concentrated almost to dryness under reduced pressure. The residue was partitioned between ethyl acetate and water. The aqueous phase was extracted three times with ethyl acetate. The combined organics were washed once with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, concentrated to dryness under reduced pressure. The residue was recrystallized from methanol to provide 4-((tetrahydro-2H-pyran-4-yl)oxy)isophthalonitrile. 1H NMR (400 MHz, DMSO-d6) delta 8.42 (d, J=2.1 Hz, 1H), 8.16 (dd, J=8.9, 2.1 Hz, 1H), 7.60 (d, J=9.0 Hz, 1H), 5.01 (m, 1H), 3.88 (m, 2H), 3.57 (m, 2H), 2.05 (m, 2H), 1.70 (m, 2H).

The synthetic route of 13519-90-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gilead Sciences, Inc.; Du, Zhimin; Guerrero, Juan A.; Kaplan, Joshua A.; Knox, JR., John E.; Lo, Jennifer R.; Mitchell, Scott A.; Naduthambi, Devan; Phillips, Barton W.; Venkataramani, Chandrasekar; Wang, Peiyuan; Watkins, William J.; Zhao, Zhongdong; (593 pag.)US2016/96827; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 143879-78-1, name is 3-Amino-2,6-difluorobenzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 143879-78-1, Computed Properties of C7H4F2N2

Example 4: 2,6-Difluoro-3-[5-(3-morpholin-4-ylphenoxy)-pyrimidin-2-ylamino]- benzonitrileA suspension of 4-[3-(2-chloro-pyrimidin-5-yloxy)phenyl]morpholine (180mg, 0.619 mmol), 3-amino-2,6-difluorobenzonitrile (95.3mg, 0.619mmol), ira(dibenzylidene- acetone)palladium(O) (28.3mg, 0.030mmol), 4,5-bis,(diphenylphosphino)-9,9- dimethyl-xanthene (35.8mg, 0.061mmol) and cesium carbonate (403mg, 1.238mmol) in degassed 1,4-dioxane (4mL) was heated at 80C for 2 days. The suspension was diluted with ethyl acetate and washed with water and brine. The organic phase was dried (MgS04) and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica (ethyl acetate:hexane, 1: 1) to afford 2,6-difluoro-3-[5-(3-morpholin-4-ylphenoxy)pyrimidin-2-ylamino]benzonitrile as a solid (l lOmg, 44%).Mass: (ES+) 410 (M+H)+ HPLC: 99.2%NMR: deltaEta ( 6-DMSO) 3.08 (4H, m), 3.69 (4H, m), 6.34 (IH, dd), 6.60 (IH, br s), 6.69 (IH, dd), 7.18 (IH, t), 7.40 (IH, t), 8.10 (IH, m), 8.35 (2H, s) and 9.59 (IH, s).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Amino-2,6-difluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SENEXIS LIMITED; HORWELL, David; SCOPES, David; WO2011/144577; (2011); A1;,
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Synthetic Route of 36764-94-0, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 36764-94-0 as follows.

General procedure: A solution of 2,4,6-trisubstitutedphenylamine (10, 0.8 mmol) in pyridine (10 mL) was added to the flask containingt he crude acyl chloride 8 (0.8 mmol) which was prepared from the procedure described above, and the mixture was refluxed for 3-5 h. After cooling down, the mixture was poured into water (50 mL) and extracted with ethyl acetate (3× 15 mL). The extracts were combined and washed with hydrochloric acid (2 × 10 mL) and brine, successively. The organic phase was dried over anhydrous Na2SO4. After solvent removal, the residue was further purified by recrystallization from ethanol to afford the title compound 12(a-c) as a solid.

According to the analysis of related databases, 36764-94-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Baolei; Wang, Hongxue; Liu, Hang; Xiong, Lixia; Yang, Na; Zhang, Yan; Li, Zhengming; Chinese Chemical Letters; vol. 31; 3; (2020); p. 739 – 745;,
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Related Products of 13726-21-1, These common heterocyclic compound, 13726-21-1, name is 2-(4-Chloro-3-methoxyphenyl)acetonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

BBr3 (17 g, 66 mmol) was slowly added to a solution of 2-(4-chloro-3-methoxyphenyl)acetonitrile (12 g, 66 mmol) in dichloromethane (120 mL) at -78 C. under N2. The reaction temperature was slowly increased to room temperature. The reaction mixture was stirred overnight and then poured into ice and water. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (40 mL*3). The combined organic layers were washed with water, brine, dried over Na2SO4, and concentrated under vacuum to give (4-chloro-3-hydroxy-phenyl)-acetonitrile (9.3 g, 85%). 1H NMR (300 MHz, CDCl3) delta 7.34 (d, J=8.4 Hz, 1H), 7.02 (d, J=2.1 Hz, 1H), 6.87 (dd, J=2.1, 8.4 Hz, 1H), 5.15 (brs, 1H), 3.72 (s, 2H).

Statistics shows that 2-(4-Chloro-3-methoxyphenyl)acetonitrile is playing an increasingly important role. we look forward to future research findings about 13726-21-1.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 27387-23-1, name is 2-(2-Bromo-5-methoxyphenyl)acetonitrile, A new synthetic method of this compound is introduced below., Product Details of 27387-23-1

D. N, N-DIMETHYL-5-METHOXY-2-BROMOPHENYLACETAMIDE 5-Methoxy-2-bromobenzoic acid (85 g, 0.37 mol) is dissolved in anhydrous THF (100 mL) and cooled in an ice-salt bath until the temperature REACHES-5 C. Borane-THF complex is added dropwise as a 1.0 M solution in THF (736 mL, 0.74 mol) AT-5C. After addition is complete, the reaction mixture is slowly warmed to room temperature and stirred for 12 hours. Water (40 mL) is slowly added dropwise and the reaction mixture stirred for 30 minutes. Additional water (350 mL) is added and the mixture is concentrated by rotary evaporator to remove most of the THF. The remaining material is extracted with EtOAc (800 mL). The organic layer is washed with saturated NAHCO3 (500 mL), brine (250 mL) and then dried (NA2SO4). UPON REMOVAL of the solvent by rotary evaporator, 5-methoxy-2- bromobenzyl alcohol is obtained as a white solid. 5-Methoxy-2-bromobenzyl alcohol (79.5 g, 0.37 mol) is dissolved in 48% HBr (400 mL) and heated to reflux temperature for 4 hours. The reaction mixture is cooled to room temperature and poured into water (1500 mL). The solution is extracted with EtOAc (2 x 500 mL). The combined organic layers are dried (MGS04) and concentrated by rotary evaporator. The crude material is then purified using flash chromatography (CH2CI2/hexanes, from 1: 1 to 4: 1) to give 5-methoxy-2-bromobenzyl bromide. 5-METHOXY-2-BROMOBENZYL bromide (72.8 g, 0.26 mol) is dissolved in EtOH (280 mL) and stirred at room temperature. Sodium cyanide (38.2 g, 0.78 mol) is dissolved in water and added to the solution of the bromide. The reaction mixture is heated to reflux temperature for 3 hours and then cooled to room temperature. Most of the ethanol is removed by rotary evaporator. A solid forms which is isolated by filtration and washed with water (500 mL). The crude material is purified using flash chromatography (CH2CI2/HEXANES, 1: 1) to give 5-methoxy-2-bromophenylacetonitrile (53 g). 5-Methoxy-2-bromophenylacetonitrile (52.8 g, 0.23 mol) is dissolved in ethanol (250 mL) and stirred at room temperature. Sodium hydroxide (9.3 g, 0.47 mol) is dissolved in water (150 mL) and added to the solution of the nitrile. The mixture is heated to reflux temperature for 12 hours and then cooled to room temperature. Most of the ethanol is removed using a rotary evaporator and the residual aqueous solution adjusted to pH 4 with 3 N HCI. The solid which forms is isolated by filtration and washed with water. Air drying gives 5-methoxy-2-bromophenylacetic acid. 5-Methoxy-2-bromophenylacetic acid (56 g, 0.23 mol) is dissolved in CH2CI2 (350 mL) and a catalytic amount of DMF is added and the solution stirred and cooled to 0C. Thionyl chloride (41 mL, 0.34 mol) is added dropwise. The reaction mixture is heated at reflux temperature overnight and then cooled to room temperature. Solvents are removed by rotary evaporator. Twice benzene (500 mL) is added to the residual oil and the benzene solution is evaporated by rotary evaporator to remove any additional volatile components. The residual oil is crystallized from hexanes to give 5-methoxy-2-bromophenylacetyl chloride. 5-Methoxy-2-bromophenylacetyl chloride (60 g, 0.23 mol) is dissolved in anhydrous ET20 (400 mL), stirred and cooled in an ice bath. A 2 M solution of DIMETHYLAMINE (228 mL, 0.46 mol) is added dropwise and the mixture allowed to warm to room temperature and stirred for 2 hours. Additional ET20 (500 mL) is added. The organic solution is washed with 1 N HCI (2 x 500 mL), saturated NAHCO3 (500 mL) and brine (500 mL). The organic layer is dried (NA2SO4) and concentrated by rotary evaporator. The residue is purified using flash chromatography (hexanes/EtOAc, from 7: 3 to 1: 9). Trituration of the crude product with ET20/HEXANES gives N, N-DIMETHYL-5-METHOXY-2-BROMOPHENYLACETAMIDE AS a white crystalline solid (m. p. 88-90C).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/48314; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 500912-18-5, name is 2-(2-Fluoro-6-methoxyphenyl)acetonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 500912-18-5, name: 2-(2-Fluoro-6-methoxyphenyl)acetonitrile

[0428] Under argon and at -78C., a mixture of 2.5 M butyllithium solution in hexane (13 ml, 33 mmol) and THF (50 ml) was added slowly to a solution of N,N-diisopropylethylamine (5.8 ml, 33 mmol) in THF (75 ml). The reaction mixture was allowed to warm to 0C., stirred at 0C. for 5 min and cooled back down again to -78C. A solution of (2-fluoro-6-methoxyphenyl)acetonitrile (5.00 g, 30.3 mmol, CAS-RN 500912-18-5, commercially available) in THF (25 ml) was then added slowly. The reaction mixture was once more allowed to warm to 0C., stirred at 0C. for 5 min and cooled back down again to -78C. A solution of iodomethane (2.0 ml, 31.79 mmol) in THF (25 ml) was then added slowly. The mixture was stirred overnight, with the temperature gradually rising to RT. At 0C., saturated ammonium chloride solution and water (50 ml each) were then added and the mixture was shaken and extracted twice with ethyl acetate (150 ml each). The combined organic phases were washed once with saturated aqueous sodium chloride solution (200 ml), dried over sodium sulfate, filtered and concentrated, and the residue was taken up in dichloromethane and purified by flash column chromatography (400 g of silica gel Buchi Snap-Cartridge KP-Sil, cyclohexane/ ethyl acetate 9:1). The combined target fractions were concentrated, and the residue was (briefly) dried under reduced pressure. This gave 3.33 g (100% purity, 61% of theory) of the title compound. [0429] GC-MS (Method 12): Rt=4.31 min; MS (ESIpos): m/z=179 [M]+ [0430] 1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 1.492 (15.85), 1.509 (16.00), 3.314 (9.13), 3.887 (0.90), 4.452 (0.69), 4.455 (0.70), 4.470 (2.12), 4.473 (2.10), 4.488 (2.11), 4.491 (2.05), 4.505 (0.69), 4.508 (0.65), 6.861 (1.62), 6.863 (1.60), 6.884 (2.45), 6.907 (1.81), 6.909 (1.81), 6.943 (3.36), 6.964 (3.72), 7.353 (1.56), 7.370 (1.87), 7.374 (2.99), 7.391 (3.02), 7.395 (1.60), 7.412 (1.36). [0431] 1H-NMR (400 MHz, DMSO-d6): 5 [ppm]=7.44-7.30 (m, 1H), 6.95 (d, 1H), 6.92-6.85 (m, 1H), 4.48 (qd, 1H), 3.88 (s, 3H), 1.50 (d,3H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-(2-Fluoro-6-methoxyphenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Aktiengesellschaft; Bayer Pharma Aktiengeseiisehaft; BECK, Hartmut; KAST, Raimund; MEININGHAUS, Mark; DIETZ, Lisa; FUERSTNER, Chantal; STELLFELD, Timo; ANLAUF, Sonja; VON BUEHLER, Clemens-Jeremias; BAIRLEIN, Michaela; ANLAHR, Johanna; MUENSTER, Uwe; TERJUNG, Carsten; JOERISSEN, Hannah; HAUFF, Peter; MUELLER, Joerg; DROEBNER, Karoline; NAGEL, Jens; (220 pag.)US2020/31775; (2020); A1;,
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Electric Literature of 72635-78-0,Some common heterocyclic compound, 72635-78-0, name is 3-Amino-4-bromobenzonitrile, molecular formula is C7H5BrN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

4-Bromo-3-chlorobenzonitrile (60c). Aniline 56 (5.19 g, 26.4 mmol) was added to conc. HCl maintained below 0 C. A solution of sodium nitrite (3.67 g, 53.2 mmol) in water (10 mL) was added dropwise such that the temperature of the reaction mixture did not exceed 5 C. The mixture was maintained for 1 h, then was added to a solution of CuCl (6.55 g, 66.2 mmol) in conc. HCl (20 mL). Toluene (200 mL) was added, and the biphasic mixture was stirred at 60-80 C for 1 h. Layers were separated, and the aqueous layer was extracted into toluene to afford a white solid (4.67 g, 82%); mp 80-81 C (hexane); 1H NMR delta 9.55 (d, J = 1.8 Hz, 1H), 8.03 (d, J = 8.4 Hz, 1H), 7.78 (d, J = 8.4 and 1.9 Hz, 1 H); HPLC (Method B) tR 3.96 min (100 area % at 265 nm). Anal. (C7H3BrClN) C, H, N, Br, Cl.; Reagents and conditions: (a) fuming HNO3, H2SO4; (b) Fe, AcOH, EtOH; (c) NaNO2, aq. HCl, then CuCl; (d) NalO4, l2, AcOH, AC2O, H2SO4; (e) NH2OH HCl, Py, EtOH (f) Ac2O; (g) TMSA, Pd2Cl2(PPh3)2, Cul, Et3N; (h) TMSA, PPh3, Pd(PPh3)4, Cul, piperidine; (j) 2-methyl-3-butyn-2-ol, Pd2Cl2(PPh3)2, Cul, Et3N; (k) 2-methyl-3-butyn-2-ol, 10% Pd/C, PPh3, Cul, aq. K2CO3/DME; (I) Cs2CO3, aq. CH3CN or MeOH; (m) NaH, toluene.; A second general method is depicted in Scheme 2 immediately hereinabove and comprises the cycloaddition of cyanophenylacetylenes 51 and benzaldehyde chlorooximes 52 in the presence of bis(tributyltin) oxide, see Moriya, O., et al., J. Chem. Soc., Perkin Trans., 1, 413-417 (1994); Moriya, O., et al., J. Chem. Soc., Chem. Commun., 17-18 (1991), or triethylamine, see Thomsen, l., et al., Acta Chem. Scand. (B), 319-313 (1988), in nonpolar solvents to give isoxazole dinitriles 53a-h,k-s and bromonitrile 53i. The latter was treated with copper(I) cyanide to give dinitrile 53j. See Friedman. L., et al., J. Org. Chem., 26, 2522-2524 (1961). This method also afforded alternate routes to dinitriles 50a,b,g, k prepared by the first method as provided in Scheme 1. The phenylacetylene synthons 51a-g were prepared as shown in Scheme 3 below. Starting materials 60a,e,g were commercially available. Nitration of 60a gave 60b. See Borsche, W., L., et al., Chem. Ber., 49, 2222-2243 (1916). The latter was reduced to aniline 56, see Blanksma, J. J., et al., Recl. Trav. Chim. Pays-Bas, 66, 365-373 (1947), which underwent diazotization followed by treatment with copper(l) chloride to give chlorobenzene 60c. Triflate 60d was prepared by treatment of 4-bromo-3-hydroxybenzonitrile with triflic anhydride. The preparation of aryl iodide 60f began with the known transformation of aldehyde 57 to iodo derivative 58. See Lulinski, P., et al., Bull. Chem. Soc. Jpn., 73(4), 951-956 (2000). Treatment of 58 with hydroxylamine hydrochloride gave aldoxime 59, which was dehydrated to give nitrile 60f using acetic anhydride. The aryl halides or triflates 60a-g were treated with (trimethylsilyl)acetylene, see Roesch. K. R., et al., J. Org. Chem., 66, 412-420 (2001), or with 2-methyl-3-butyn-2-ol, see Bleicher, L. S., et al., J. Org. Chem., 63, 1109-1118 (1998), to give intermediates 61a-f or 62a-f, respectively, of which 61a,d and 62a have been reported previously. See Dirk. S. M., et al., Tetrahedron, 59(3), 287-293 (2003); Bleicher, L. S., et al., J. Org. Chem., 63, 1109-1118 (1998). The acetylenes 51 (of which 51a,e were known previously), see Blackburn, B. K., et al., J. Med. Chem., 40(5), 717-729 (1997); Dulog, L., et al., Liebigs Ann. Chem., 9, 1663-1671 (1995), were obtained by the treatment of intermediates 61 or 62 with cesium carbonate in acetonitrile or sodium hydride in toluene, respectively. See Bleicher, L. S., et al., J. Org. Chem., 63, 1109-1118 (1998). The use of cesium carbonate in acetonitrile was introduced for the deprotection of intermediates 61 after the treatment of compound 61b with potassium carbonate in methanol, see Blackburn, B. K., et al., J. Med. Chem., 40(5), 717-729 (1997), failed to give product 51b. The pathway using 2-methyl-3-butyn-2-ol provided more economical preparations of all phenylacetylenes 51 except nitro analog 51b.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Amino-4-bromobenzonitrile, its application will become more common.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; EP1719767; (2006); A1;,
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Reference of 251570-03-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 251570-03-3 name is 2-(4-Chloro-3-fluorophenyl)acetonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A mixture of the product of example 22 (7.8g, 0.046 mol), water (7.5 ml), concentrated sulfuric acid (7.5ml) and acetic acid (7.5ml) was heated at reflux for 2 hours . After being cooled to room temperature, the mixture was poured into ice-water. The resulting solids were collected by filtration and washed by diethyl ether to give the titled product (6.8g, 79%)1H NMR (300 MHz, DMSO-/) 3.64 (s, 2H), 7.14 (ddd, J= 0.6, 2.1, 8.2 Hz, IH), 7.34 (dd, J= 2.1, 10.6 Hz, IH), 7.52 (t, J=8.1 Hz, IH).MS (ESI”) m/z 187 (M-I)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Chloro-3-fluorophenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; AVEXA LIMITED; DEADMAN, John, Joseph; JONES, Eric, Dale; LE, Giang, Thanh; RHODES, David, Ian; THIENTHONG, Neeranat; VAN DE GRAFF, Nicholas, Andrew; WINFIELD, Lisa, Jane; WO2010/31; (2010); A1;,
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Related Products of 70484-02-5,Some common heterocyclic compound, 70484-02-5, name is 6-Bromonaphthalene-2,3-dicarbonitrile, molecular formula is C12H5BrN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Synthetic Example 28 [Synthesis of 2,3-dicyano-6-(3′,5′-dimethoxycarbonylphenylthio)naphthalene] 10 Grams (38.9 mmols) of the 6-bromo-2,3-dicyanonaphthalene obtained in Synthetic Example 2 and 12.9 g (44.7 mmols) of copper (I) 3,5-dimethoxycarbonylphenylthiolate were stirred in 200 ml of quinoline at 160 C. for 10 hours. After cooling, the reaction mixture was poured into 600 ml of methanol/water (1/1) and the resulting mixture was allowed to stand overnight. The precipitate formed was filtered and sufficiently washed with methanol. The solid thus obtained was transferred to a Soxhlet extractor and extracted with acetone for 20 hours. The acetone solution thus obtained was concentrated, after which methanol was added and the solid precipitated was filtered and sufficiently washed with methanol. The solid thus treated was purified by a silica gel column chromatography (eluent: ethyl acetate) and then recrystallized from acetone to obtain 4.32 g of colorless crystals. The crystals were confirmed to be 2,3-dicyano-6-(3′,5′-dimethoxycarbonylphenylthio)naphthalene from the following analysis results:

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromonaphthalene-2,3-dicarbonitrile, its application will become more common.

Reference:
Patent; Hitachi Chemical Company; US5438135; (1995); A;,
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Related Products of 86770-80-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 86770-80-1, name is 3,3-Difluorocyclobutanecarbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 125C 3,3-difluoro-1-(4-(trifluoromethyl)pyridin-2-yl)cyclobutanecarbonitrile Example 125B and 2-fluoro-4-(trifluoromethyl)pyridine (0.900 mL, 7.39 mmol) were dissolved in toluene (2.4 mL), cooled to <5 C. and added KHMDS (29.6 mL, 14.78 mmol) dropwise, allowed to warm slowly to room temperature and stirred for 90 minutes. The mixture was diluted with MTBE and washed with water (2*). The organic phase was dried (Na2SO4), filtered, and concentrated. The residue was chromatographed on silica gel (0-25% EtOAc/hexanes) to provide Example 125C (1.22 g, 4.65 mmol, 63.0% yield). 1H NMR (300 MHz, DMSO-d6) delta 9.00-8.94 (m, 1H), 8.04-7.99 (m, 1H), 7.88 (ddd, J=5.1, 1.6, 0.8 Hz, 1H), 3.68-3.48 (m, 5H). The synthetic route of 3,3-Difluorocyclobutanecarbonitrile has been constantly updated, and we look forward to future research findings. Reference:
Patent; AbbVie Inc.; Bayburt, Erol K.; Clapham, Bruce; Cox, Phil B.; Daanen, Jerome F.; Dart, Michael J.; Gfesser, Gregory A.; Gomtsyan, Arthur; Kort, Michael E.; Kym, Philip R.; Schmidt, Robert G.; Voight, Eric A.; US2014/80803; (2014); A1;,
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