Month: May 2021

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. 4387-32-0, name is 2-Chloro-5-methylbenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Chloro-5-methylbenzonitrile

To a solution of 2-chloro-5-methyl-benzonitrile (9.0 g, 59.4 mmol) in anhydrous THF (90 mL) at 0 C was added BH3-THF (1.0 M, 178 mL, 178 mmol) dropwise under a nitrogenatmosphere. The mixture was stirred at room temperature for 12 h. The reaction was quenched with 2N HC1 (110 mL) at 0 C and then heated to 70 C for 1 h. After cooling the reaction to room temperature, the solution was washed with DCM (150 mL). The aqueous phase was basified with iN NaOH to pH 8 and then extracted with DCM (150 mL x 3). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give thetitle compound (5.8 g, 63%) as yellow oil. ?HNMR (400 IVIFIz, CDC13) 7.22 (d, J 8.0 Hz,1H), 7.17 (s, 1H), 6.99 (d, J= 8.0 Hz, 1H), 3.88 (s, 2H), 2.32 (s, 3H).

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; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy M.; WAI, John; LAI, Kwong Wah; WANG, Fei; CHEN, Kevin X.; (351 pag.)WO2017/205538; (2017); A1;,
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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 133541-45-4 as follows. Computed Properties of C7H2BrF2N

To a stirred suspension of 4-bromo-2,5-difluorobenzonitrile (91 g, 417 mmol) and potassium carbonate (173 g, 1.25 mol) in N,N-dimethylformamide (910 ml) was added (S)-l,l,l- trifluoropropanol [CAS 3539-97-7] dropwise (52.4 g, 460 mmol). The resulting mixture was heated at 70 C for for 15 hours and cooled to room temperature. The reaction was concentrated and the residue was diluted with water. The aqueous solution was extracted with DCM (3x). The combined organic washes were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give an oil (136.6 g). The residue was triturated with a mixture of hexanes and toluene (9:1, 200 mL) to give the desired product as a white solid (90.3 g, 93% purity, 64% yield). LC-MS (Method A): R, = 1.29 min; MS (ESIpos): m/z = 312.0 [M+H]+. 1H-NMR (400 MHz, CHLOROFORM-d) d [ppm] : 1.511 (4.41), 1.531 (15.64), 1.533 (16.00), 1.548 (15.84), 1.550 (15.83), 4.566 (1.08), 4.581 (2.68), 4.597 (3.18), 4.612 (2.62), 4.626 (1.01), 7.194 (5.27), 7.207 (7.60), 7.220 (7.57).

According to the analysis of related databases, 133541-45-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; JANZER, Andreas; POLITZ, Oliver; EHEIM, Ashley, Lakner; (87 pag.)WO2019/197269; (2019); 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. 508203-48-3, name is 2,3-Difluoro-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 508203-48-3

To a suspension of 2,3-difluoro-4-methylbenzonitrile (5.0 g, 32.6 mmcl) in ethanol (111 mL) at25C was added hydroxylamine hydrochloride (4.5 g, 65.3 mmol). The reaction mixture was heated at80C for 2 hours. After cooling to room temperature, the volatiles were removed under reduced pressurethus affording a white solid that was used in the next transformation without purification.1H NMR (400 MHz, CDCI3) oe ppm: 7.30 (m, 1H), 6.95 (m, 1H), 6.50 (brs, 1H), 5.05 (brs, 2H),2.30 (s, 3H).

According to the analysis of related databases, 508203-48-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; HOFFMAN, Thomas, James; STIERLI, Daniel; BEAUDEGNIES, Renaud; POULIOT, Martin; HAAS, Ulrich, Johannes; (161 pag.)WO2018/177894; (2018); 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. 13726-21-1, name is 2-(4-Chloro-3-methoxyphenyl)acetonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(4-Chloro-3-methoxyphenyl)acetonitrile

(4-Chloro-3-hydroxy-phenyl)acetonitrile 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).

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; Vertex Pharmaceuticals Incorported; US2011/98311; (2011); A1;,
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Electric Literature of 191014-55-8, A common heterocyclic compound, 191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile, molecular formula is C8H6FNO, 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 solution of 1 g of 4-fluoro-2-methoxy-benzonitrile in 15 mL of dichloroethane was added 1.1 g of aluminum trichloride. The resulting mixture was refluxed for 1 day then poured slowly into water and extracted with ethyl acetate. The organic extracts were washed twice with 10% aqueous solution of sodium hydroxide. The combined basic layers were washed twice with ethyl acetate, acidified with concentrated aqueous solution of hydrochloric acid and extracted three times with ethyl acetate. The combined organic extracts were washed with water, with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 0.78 g of 4-fluoro-2-hydroxy-benzonitrile as a white solid.C7H4FNO (137.11), MS (ESI): 138.17 (M+H+).

The synthetic route of 191014-55-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; US2008/261979; (2008); A1;,
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Synthetic Route of 2947-60-6, 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. 2947-60-6 name is 3-Methylbenzyl cyanide, 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.

Example 1 Synthesis of 1-methoxy-2-(3-methylphenyl)ethanimine (Compound 1) Cold 4 M hydrogen chloride in dioxane (184 ml, 0.763 mol) is added to a stirred and cooled (0 C.) mixture of 3-methylbenzyl cyanide (25 g, 0.19 mol) in anhydrous methanol (23 ml, 0.57 mol) and anhydrous ether (100 ml). The resulting reaction mixture is stirred at 0 C. for an additional hour and then it is placed in a refrigerator (0-5 C.) for 48 hours (during this time a small amount of white crystalline material precipitated). The reaction mixture is removed from the refrigerator and warmed to approximately 40 C. using a warm water bath. Nitrogen gas is then bubbled through the warm reaction mixture to remove excess hydrogen chloride. The volume of the solvent is reduced in vacuo, and anhydrous ether is added to effect precipitation. The precipitate is collected by filtration, washed with ether and dried under vacuum to afford 31 g (82%) of the crystalline imidate hydrochloride salt (1) as a white solid. 1H NMR (CDCl3): delta 12.82 (br s, 1H), 11.85(br s, 1H), 7.0-7.25(m, 5H), 4.25 (s, 3H), 4.0(s, 2H), 2.31 (s, 3H). 13C NMR (CDCl3): delta 178.7, 139.3, 131.2, 130.5, 129.5, 129.3, 126.9, 61.3, 39.3, 21.6.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methylbenzyl cyanide, and friends who are interested can also refer to it.

Reference:
Patent; Kolb, Hartmuth C.; Kanamarlapudi, Ramanaiah C.; Richardson, Paul F.; Khan, Gaznabi; US2003/153728; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 41429-22-5, name is 2-(2-(Difluoromethoxy)phenyl)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 41429-22-5, Formula: C9H7F2NO

Synthesis of ethyl (2-difluoromethoxyphenyl)acetate (2-Difluoromethoxyphenyl)acetonitrile (1.45 g) was added dropwise to a solution of chlorotrimethylsilane (2.23 mL) in ethanol (2.0 mL), and the reaction solution was stirred at 50C for five hours. The reaction solution was left to cool to room temperature. Then, potassium carbonate, water and ethyl acetate were added and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 620 mg of the title compound. The property values of the compound are as follows. 1H-NMR (CDCl3) delta (ppm): 1.26 (t, J=7.2Hz, 3H), 3.68 (s, 2H), 4.16 (q, 7.2Hz, 2H), 6.48 (t, J=74.4Hz, 1H), 7.13-7.32 (m, 4H).

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-(Difluoromethoxy)phenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2181992; (2010); 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. 1735-54-2, name is 4-Chloro-3-(trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., name: 4-Chloro-3-(trifluoromethyl)benzonitrile

a) 4-Chloro 3-trifluoromethyl-benzamidoxime The title compound was prepared from 4-chloro-3-trifluoromethyl-benzonitrile (617 mg, 3.00 mmol) and 0.576 M hydroxylamine hydrochloride in 95% ethanol (5.8 mL, 3.3 mmol) similar to Example 36c, and yielded 528 mg (74%) of white solid. 1H NMR (Acetone-d6): 9.29 (s, 1H), 8.15 (d, J=2.19 Hz, 1H), 8.00 (m, 1H), 7.69 (d, J=8.24 Hz, 1H), 5.73 (s, 2H).

The synthetic route of 1735-54-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cai, Sui Xiong; Zhang, Han-Zhong; Drewe, John A.; Reddy, P. Sanjeeva; Kasibhatla, Shailaja; Kuemmerle, Jared Daniel; Ollis, Kristin P.; US2003/45546; (2003); A1;,
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Synthetic Route of 20925-24-0, 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. 20925-24-0, name is 2-(Dimethylamino)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred mixture of FeCl36H2O (270.3 mg, 1.0 mmol) and2.0 mL toluene was added aniline 1 (0.4 mmol) at room temperature.The reaction mixture was stirred at 85 C for 2 h in atmosphere.After it was cooled to room temperature, the reactionmixture was quenched by aqueous ammonia solution (mass fraction:25e28%, 10 mL) and extracted with dichloromethane (10 mLper time) until no product was observed in the extract, monitoredby TLC. The organic layer was dried over anhydrous MgSO4, filtered,and concentrated under reduced pressure to give crude product,which was chromatographed on silica gel column using 1:100 to1:70 (v/v) EtOAc/petroleum ether solutions as eluent to affordisolated product 2.

The synthetic route of 2-(Dimethylamino)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pan, Jing; Li, Jiaqiang; Huang, Ruofeng; Zhang, Xiaohui; Shen, Hang; Xiong, Yan; Zhu, Xiangming; Tetrahedron; vol. 71; 33; (2015); p. 5341 – 5346;,
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Electric Literature of 886500-41-0,Some common heterocyclic compound, 886500-41-0, name is 4-Chloro-2,6-difluorobenzonitrile, molecular formula is C7H2ClF2N, 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.

A mixture of 4-chloro-2,6-difluorobenzonitrile (1.66 g, 9.56 mmol), pyrrole (0.67 g, 10 mmol) and Cs2CO3 (3.7 g, 12 mmol) in DMF (20 ml) was stirred overnight. Then, the solid was filtered off and the solvent was removed by reduced pressure. The residue was purified by column chromatography over silica gel (eluent: EtOAc/petroleum ether 10/1). The desired fractions were collected and the solvent was evaporated. Yield: 1.1 g of intermediate 15 (15% yield; white solid).

The synthetic route of 886500-41-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Meerpoel, Lieven; Maes, Louis Jules Roger Marie; de Wit, Kelly; US2013/85136; (2013); A1;,
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