Tag: M.W=200-300

Related Products of 1813-33-8, These common heterocyclic compound, 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, 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.

To commercially available 2-chloro-4-trifluoromethylbenzonitrile 13 (0.5 ml, 3.6 mmol) dimethylamine (4equiv., 0.95 ml) was added and the solution was heated in closed vessel at 80C overnight. The reaction was evaporated and the residue was dissolved in AcOEt and washed with water and brine. The organic phase was evaporated obtaining 730 mg of a pale yellow oil. Yield = 94% ‘HNMR (CDC13, 200 MHz) delta 3.13 (6H, s), 7.05 (1H, bs), 7.59 (1H, dd, J = 8.4 Hz, J’ = 0.6 Hz), 7.99 (1H, bs)

Statistics shows that 2-Chloro-4-(trifluoromethyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 1813-33-8.

Reference:
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); A1;,
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Related Products of 1261609-83-9, These common heterocyclic compound, 1261609-83-9, name is 2-Bromo-5-(hydroxymethyl)benzonitrile, 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.

Step B: Preparation of 2-bromo-5-(chloromethyl)benzonitrile [00231] To a magnetically stirred mixture of 2-bromo-5-(hydroxymethyl)benzonitrile (0.5 g, 2.358 mmol) in dry DCM (11.79 ml) at ice-bath tetmperatures was added thionyl chloride (0.344 ml, 4.72 mmol) in a dry 50 mL round-bottomed flask. DMF (0.5 mL) was added to aid solubilization. The reaction mixture was stirred at reduced temperature for 15 min and then was allowed to warm to rt. After 1 h, GC-MS analysis indicated the reaction was complete. The reaction mixture was diluted with DCM and sat’d aq. NaHC03, then stirred vigorously for 30 min. The layers were separated, the aq layer was extracted again with DCM, and the combined DCM extracts were dried over sodium sulfate, and filtered through a phase separator. The DCM was evaporated to afford 485 mg (56%) of the title compound as a white wax. H NMR (400 MHz, CDCI3) delta 7.70 (d, J = 3.8 Hz, 1H), 7.68 (d, J = 2.1 Hz, 1H), 7.48 (dd, J = 8.4, 2.3 Hz, 1H), 4.54 (s, 2H). 13C NMR (101 MHz, CDC13) delta 137.70, 134.03, 133.82, 133.60, 125.14, 116.62, 116.36, 43.93. GC-MS m z 231.

The synthetic route of 1261609-83-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; LOSO, Michael R.; GUSTAFSON, Gary D.; KUBOTA, Asako; YAP, Maurice C.; BUCHAN, Zachary A.; STEWARD, Kimberly M.; SULLENBERGER, Michael T.; HOEKSTRA, William J.; YATES, Christopher M.; WO2015/160665; (2015); A1;,
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Electric Literature of 36282-26-5, A common heterocyclic compound, 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

To a stirred solution of 2-bromo-4-fluorobenzonitrile (5 g, 25 mmol) and Ti(Oi-Pr)4 (9.05 mL, 27.5 mmol) in ether (100 mL) at -78 C was added EtMgBr (18.3 mL,55 mmol) drop wise. The solution was allowed to warm to room temperature and stirred for 1 hour before BF3-Et20 (6.25 mL) was added and stirring continued at room temperature for another 1 hour. The reaction solution was quenched with 1 N HC1 solution, and washed with EtOAc. The aqueous layer was adjusted to pH~10 with aq. NaOH (2 N) solution and then exacted with EtOAc (3 x). The combined organic layers were dried over anhy.Na2S04, filtered, and concentrated in vacuo. The residue was then purified by column chromatography to give title compound (3.0 g, yield 52.2%) as yellowish oil.

The synthetic route of 36282-26-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
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Reference of 160892-07-9, The chemical industry reduces the impact on the environment during synthesis 160892-07-9, name is 5-Bromoisophthalonitrile, I believe this compound will play a more active role in future production and life.

In a nitrogen atmosphere5-Bromoisophthalonitrile (30.0 g, 144.9 mmol)And (3,5-dichlorophenyl) boronic acid (30.4 g, 159.4 mmol)Were added to 400 ml of tetrahydrofuran, and the mixture was stirred and refluxed.After this, potassium carbonate (60.1 g, 434.7 mmol)In 180 ml of waterAfter thoroughly stirring, tetrakistriphenyl-phosphinopalladium (5.0 g, 4.4 mmol) was added thereto. After 8 hours of reaction, the temperature was lowered to room temperature and filtered.The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate.The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate.The resulting solid was filtered and dried to give Compound 5A (30.5 g, 77%).

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, 5-Bromoisophthalonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LG CHEM, LTD.; JUNG, Min Woo; LEE, Dong Hoon; HUH, Jung oh; JANG, Boon jae; KANG, Min young; HEO, Dong Uk; HAN, Mi yeon; (26 pag.)KR2017/92131; (2017); A;,
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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 66389-80-8 as follows. category: nitriles-buliding-blocks

Synthesis of SiR-Tz (FIG. 8) (0148) 4-Cyanobenzylamine HCl was Boc-protected with Boc-anhydride. The Boc-protected amine was converted to the tetrazine 8 (Yang, et al., 2012, Angew. Chem., Int. Ed. 51:5222-5225). The Boc-group of tetrazine 8 was removed by treating the compound with a 1:1 mixture of TFA and dichloromethane and immediately coupled with SiR-OH (Lukinavicius, et al., 2013, Nature Chem. 5:132-139) mediated by TBTU and iPr2NEt.

According to the analysis of related databases, 66389-80-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yale University; ERDMANN, Roman; SHRADER, Alanna Schepartz; TOOMRE, Derek; (34 pag.)US2016/115180; (2016); A1;,
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Synthetic Route of 914250-82-1, 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 914250-82-1 as follows.

3-bromo-2-chlorobenzonitrile (500 mg, 2.30 mmol), bis(pinacolato)diboron (741 mg, 2.92 mmol), [l,l ‘-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with DCM (93.9 mg, 115 muiotaetaomicron) and potassium acetate (689 mg, 7.03 mmol) were weighed into a 40 ml vial equipped with a teflon/rubber screw cap and a stir bar. The reaction vessel was purged 3 times with N2, dioxane (degassed) (18.4 mL) was added against N2 and the headspace of the reaction was purged 3 more times with N2. The reaction was placed into a heating block preheated to 85 C and stirred vigorously at this temperature for 2.5 hours. After cooling to room temperature the mixture was filtered over celite, the filtrate was evaporated to dryness and the crude product was purified by column chromatography (0 – 99% EtO Ac/heptanes) to give 370 mg (61%) of the desired product. LC-MS (ESI) m/z: [M + H] calculated for CI3HI5BC1N02: 264.10, found 263.8.

According to the analysis of related databases, 914250-82-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; REVOLUTION MEDICINES, INC.; JOGALEKAR, Ash; WON, Walter; KOLTUN, Elena S.; GILL, Adrian; MELLEM, Kevin; AAY, Naing; BUCKL, Andreas; SEMKO, Christopher; KISS, Gert; (496 pag.)WO2018/13597; (2018); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 50743-32-3, name is 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 50743-32-3

REFERENCE EXAMPLE b 1 In carbon tetrachloride (300 ml) was suspended 6-isopropyl-4-oxo-4H-1-benzopyran-3-carbonitrile (10.65 g). To the suspension was added N-bromosuccinimide (8.90 g). The mixture was subjected to reflux for two hours under irradiation of infrared ray lamp (Toshiba, 100 V, 375 WR). The resultant was then cooled to room temperature, followed by removal of insolubles by filtration. The filtrate was concentrated under reduced pressure. The concentrate was dissolved in ethyl acetate (150 ml), which was washed with water three times, dried and concentrated. The precipitating crystals were collected by filtration to give 6-(1-bromo-1-methylethyl)-4-oxo-4H-1-benzopyran-3-carbonitrile as colorless prisms (7.0 g). Melting point: 115-117 C.

According to the analysis of related databases, 50743-32-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US4716167; (1987); A;,
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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. 872091-83-3, name is Methyl 4-chloro-3-(cyanomethyl)benzoate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 872091-83-3

Step 3: Intermediate 3 [00778j To a solution of Intermediate 2 (920 mg, 4.41 mmol) in MeOH (10 mL) was added H2S04 (4 mL) at 25 C. The mixture was allowed to stir at 60 C for 16 h. The mixture was basified with saturated aqueous Na2CO3 to pH 8 and extracted with DCM. The combined organic layers were dried over anhydrous Na2SO4 and concentrated to afford the title compound as off- white solid (910 mg, 86%). ?H NMR (400 MHz, CDC13): oe 7.97 (d, 1H), 7.46 (d, 1H), 7.90 (dd, 1H), 3.91 (s, 3H), 3.83 (s, 2H), 3.72 (s, 3H).

The synthetic route of 872091-83-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; SANOFI; D’AGOSTINO, Laura Akullian; SJIN, Robert Tjin Tham; NIU, Deqiang; MCDONALD, Joseph John; ZHU, Zhendong; LIU, Haibo; MAZDIYASNI, Hormoz; PETTER, Russell C.; SINGH, Juswinder; BARRAGUE, Matthieu; GROSS, Alexandre; MUNSON, Mark; HARVEY, Darren; SCHOLTE, Andrew; MANIAR, Sachin; WO2014/144737; (2014); 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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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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