Author: Jessica.F

Related Products of 75344-77-3, The chemical industry reduces the impact on the environment during synthesis 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, I believe this compound will play a more active role in future production and life.

Under a nitrogen atmosphere, Add 2.52 g (12 mmol) to a 250 ml three-neck round bottom reaction flask4-bromo-3,5-dimethylbenzonitrile and 2.814 g (16 mmol) of 4,4,5,5-tetramethyl-2-(3,4,5-trifluorophenyl)-1,3, 2-dioxaborolan,Then, 120 ml of toluene, 50 ml of ethanol was added, and then 40 ml of a saturated solution of potassium carbonate (2 mol/L) was added and stirred. After 15 minutes of aeration, tetrakis(triphenylphosphine)palladium 100 mg (0.087 mmol) was added and aeration was continued for 15 minutes. The reaction system was heated to 85 C and stirred at reflux overnight.After the reaction was stopped to return to room temperature, the solvent of the reaction system was removed by rotary evaporation. The reaction system was extracted with dichloromethane and washed three times with deionized water and three times with brine.The product was purified by column chromatography using a mixture of petroleum ether and dichloromethane in a ratio of 3:1.Finally, 2.8 g of a white solid 3′,4′,5′-trifluoro-2,6-dimethyl-[1,1′-biphenyl]-4-carbonitrile (intermediate product) was obtained.The yield was 89.2%.

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, 4-Bromo-3,5-dimethylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; South China University of Technology; Su Shijian; Cai Xinyi; Qiu Weidong; Qiao Zhenyang; (32 pag.)CN108530376; (2018); A;,
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Related Products of 658-99-1, These common heterocyclic compound, 658-99-1, name is 2-(3,4-Difluorophenyl)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.

Methyl (3R,4R)-3-(3-chlorophenyl)-4-cyano-4-(3,4-difluorophenyl)butanoate (Table 1, Example 10) [0772] RRN 13a) Preparation of the diastereomeric methyl 3-(3-chlorophenyl)-4-cyano-4-(3,4-difluorophenyl)butanoates: [0773] Under protective gas (Ar), 0.779 g (5.086 mmol) of (3,4-difluorophenyl)acetonitrile and 0.1 ml of sodium methoxide solution (30% in methanol) were added to 1.000 g (5.086 mmol) of methyl 3-(3-chlorophenyl)acrylate in 12.0 ml of methanol, and the mixture was stirred in a closed vessel in a microwave oven at 100 C. for 4 h. The solvent was removed under reduced pressure, the residue was taken up in dichloromethane and the mixture was washed twice with in each case 25 ml of water. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Chromatography of the residue on silica gel (ethyl acetate/heptane=20:80) gave 0.738 g (37% of theory) of the diastereomeric methyl 3-(3-chlorophenyl)-4-cyano-4-(3,4-difluorophenyl)butanoate (erythro:threo=43:57, comparison of the doublets in the 1H-NMR in CDCl3 at 4.40 and 4.08 ppm).

Statistics shows that 2-(3,4-Difluorophenyl)acetonitrile is playing an increasingly important role. we look forward to future research findings about 658-99-1.

Reference:
Patent; Jakobi, Harald; Mosrin, Marc; Gatzweiler, Elmar; Haeuser-Hahn, Isolde; Heinemann, Ines; Rosinger, Christopher Hugh; Angermann, Alfred; Hoffmann, Michael Gerhard; Schnatterer, Stefan; Zeiss, Hans-Joachim; US2014/194291; (2014); A1;,
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Application of 69395-13-7, These common heterocyclic compound, 69395-13-7, name is 4-(2-Hydroxyethyl)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 a solution of 4- (2-hydroxyethyl) benzonitrile (10.0 g, 67.94 mmol) in CH2CL2 (175 ML) at 0C was added Et3N (11.36 mL, 8.25 mmol) and MSCL (6.31 mL, 81.53 mmol). After stirring at 0C for 3.5 hours, the reaction was poured into water (100 ML) and separated. Organic layer was dried over NA2SO4, filtered and concentrated in vacuo. Crude residue was dissolved in DMF (100 mL) and NaN3 (9.15g, 140.72 mmol) and water (5 ML) were added. The resulting solution was heated to 125C. After overnight stirring at 125C, the crude reaction mixture was cooled, diluted with EtOAc (200 mL) and poured into water (150 ML). Organic layer was washed with water (5 x 150 mL), dried over sodium sulfate, filtered, and concentrated to give 4- (2-azidoethyl) benzonitrile which was used without purification. A solution of 4- (2-azidoethyl) benzonitrile (500 mg, 2.90 mmol) in 1: 1 ETOH/ETOAC (3 mL) at 0C was purged with N2. Then Pd/C (440 mg) was added and a H2 balloon was placed over the reaction. After stirring at 0C for two hours, the reaction mixture was filtered through a pad of celite and concentrated to give 4- (2-aminoethyl) benzonitrile, which was used without further purification. LCMS (ES) 147.3 m/z (M + H) +.

The synthetic route of 69395-13-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2004/54584; (2004); A1;,
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Electric Literature of 4110-35-4, 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 4110-35-4 as follows.

3,5-dinitro-benzonitrile (3 g, 16 mmol), 6-methylpyridin-3-ol (1.7 g, 16 mmol), and K2CO3 (4.3 g, 31 mmol) were dissolved in DMF and heated to 1 10 C overnight. The reaction mixture was poured into water and the mixture was extracted with EtOAc. The combined organics were washed with brine, dried (Na2S04), concentrated in vacuo and purified by silica gel chromatography to provide 3-(6- methylpyridin-3-yloxy)-5-nitrobenzonitrile (3 g, 76% yield ). FontWeight=”Bold” FontSize=”10″ H NMR (400 MHz, DMSO) delta 8.50 (s, 1 H), 8.38 (s, 1 H), 8.08 (s, 1 H), 8.01 (s, 1 H), 7.59-7.56 (d, J = 10 Hz, 1 H), 7.38-7.36 (d, J = 8.4 Hz, 1 H), 1.98 (s, 3 H); MS (ESI) m/z: 256.3 [M+H]+.

According to the analysis of related databases, 4110-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; FLYNN, Daniel L.; PETILLO, Peter A.; KAUFMAN, Michael D.; WO2013/36232; (2013); A2;,
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Synthetic Route of 64248-62-0, These common heterocyclic compound, 64248-62-0, name is 3,4-Difluorobenzonitrile, 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.

(2) Methyl2-[[(2R)-1-hydroxy-3-phenylpropan-2-yl]amino]-5-methyl-4-thiazole carboxylate (200 mg, 0.65 mmol) was dissolved in dimethyl acetamide (13 mL) and sodium hydride (60% in oil, 109 mg, 1.63 mmol) was added, and the mixture was stirred at 0 C. To this solution was added 3,4-difluorobenzonitrile (272 mg, 1.96 mmol), and the mixture was stirred at 0 C. for 15 minutes. To the solution was added an ammonium chloride aqueous solution and the mixture was extracted with ethyl acetate twice. The organic fraction was washed with a saturated salt solution and dried over sodium sulfate. The solvent was removed by distillation under reduced pressure and the resultant residue was purified by column chromatography to obtain methy 2-(4-cyano-2-fluoro-N-[(2R)-1-hydroxy-3-phenylpropan-2-yl]anilino)-5-methyl-4-thiazole carboxylate (119 mg, 43%) as a white solid. 1H-NMR (CDCl3) delta: 7.42-7.38 (2H, m), 7.32-7.20 (5H, m), 7.06 (1H, t, J=8.5 Hz), 5.26-5.23 (1H, brm), 4.14-4.08 (3H, m), 3.88 (3H, s), 3.12-3.10 (2H, brm), 2.61 (3H, s).

The synthetic route of 64248-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Teijin Pharma Limited; HOSODA, Shinnosuke; UNOKI, Gen; WATANABE, Hidekazu; SASAKI, Kosuke; SHIBATA, Jun; YOKOYAMA, Emi; HORIE, Kyohei; TAKAGI, Kenichiro; (202 pag.)US2019/31628; (2019); A1;,
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Application of 77-57-6, These common heterocyclic compound, 77-57-6, name is 1-Phenylcyclopentanecarbonitrile, 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.

1-phenylcyclopentane-1-carbonitrile (1.530 g, 8.935 mmol) prepared in step 1 and polyphosphoric acid (115.00%, 5mL) mixed at room temperature after stirring at 110 C for 17 hours, the reaction was terminated by lowering the temperature to room temperature. The mixture was slowly added to a saturated aqueous solution of sodium bicarbonate (300 mL) at 0 C and then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and water was removed with anhydrous magnesium sulfate, followed by filtration and concentration under reduced pressure. Ethyl acetate (10 mL) was added to the concentrate, and the precipitated solid was stirred and washed with ethyl acetate and dried to give the title compound (1.340 g, 79.2%) as a white solid.

The synthetic route of 77-57-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chong Kun Dang Co., Ltd.; Kim, Yoon Tae; Lee, Chang Sik; Oh, Jung Taek; Song, Hey Sung; Choe, Jin; Lee, Jae Young; (210 pag.)KR2017/43091; (2017); A;,
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Electric Literature of 4107-65-7, 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. 4107-65-7, name is 2,4-Dimethoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1 8-(2,4-Dimethoxy-phenyl)-purine A mixture of 2 g of 4,5-diamino-pyrimidine, 4 g of 2,4-dimethoxy-benzonitrile, 6 g of p-toluene sulfonic acid hydrate, and 40 ml of benzene was heated, whereby the benzene was distilled off. The residue was heated for 30 minutes at 120 C. After cooling the residue was triturated with 2 N ammonia and extracted with ethyl acetate. The ethyl acetate phase was extracted with 2 N hydrochloric acid, the aqueous phase was neutralized and again extracted with ethyl acetate, and subsequently the organic phase was extracted with 2 N sodium hydroxide solution. When the aqueous phase was neutralized, the product was precipitated and recrystallized from water. Yield: 0.15 g (3% of theory), M.P.: 221 C. (decomp).

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, 2,4-Dimethoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim Gesellschaft mit beschrankter Haftung; US4299834; (1981); 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. 1223434-15-8, name is Methyl 4-bromo-2-cyanobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 4-bromo-2-cyanobenzoate

A mixture of Compound II (980 mg), 2N aqueous lithium hydroxide solution (6.1 mL) and methanol (18 mL) was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure, and to the residue was added 1N aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The aqueous layer was acidified with 4N hydrochloric acid, and then extracted with chloroform. The chloroform layer was dried over sodium sulfate, and then concentrated under reduced pressure to give Compound III (808 mg).

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; Dainippon Sumitomo Pharma Co., Ltd.; HORIUCHI, Yoshihiro; FUJIWARA, Hiroaki; SUDA, Hitoshi; SASAKI, Izumi; IWATA, Mitsutaka; SAWAMURA, Kiyoto; EP2612848; (2013); A1;,
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Reference of 633336-81-9, These common heterocyclic compound, 633336-81-9, name is 4-(Aminomethyl)-3,5-difluorobenzonitrile, 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.

A solution of 4-aminomethyl-2,6-difluorobenzonitrile (0. [876] g, 5.21 mmol; see step (vi) above) was dissolved in 50 mL of THF and di-tert-butyl dicarbonate (1.14 g, 5.22 mmol) in 10 mL of THF was added. The mixture was stirred for 3.5 h. The THF was evaporated and the residue was partitioned between water and EtOAc. The organic layer was washed three times with 0.5 M HCI and water, dried (Na2SO4) and evaporated. The product could be used without further purification. Yield: 1. 38 g (99%). [‘H] NMR (300 MHz, [CDC13)] 8 7.21 (m, 2H), 4.95 (broad, 1H), 4.43 (broad, 2H), 1.52 (s, 9H)

The synthetic route of 633336-81-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2003/101957; (2003); A1;,
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Related Products of 17417-09-3, 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 17417-09-3 as follows.

Example 11 1-(3′-Aminobenzisoxazol-5′-yl)-3-methyl-5-[(2′-aminosulfonyl-[1,1′]-biphen-4-yl)aminocarbonyl]pyrazole To a solution of 2-fluoro-5-nitrobenzonitrile (2.0 g) in ethylacetate (50 mL) was added stannous chloride dihydrate (27.0 g). The mixture was brought to reflux for 1.5 h and allowed to cool. The mixture was partitioned between ethyl acetate and sodium bicarbonate (sat. in water). The aqueous phase was extracted with ethyl acetate four times. The organic phase was washed with 4xH2O, dried over sodium sulfate, filtered and concentrated to leave 4-fluoro-3-cyanoaniline (1.40 g). CI mass spectrum z (rel. intensity) 137 (M+H, 100).

According to the analysis of related databases, 17417-09-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Pharma Company; EP991638; (2005); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts