Category: 147754-12-9

These common heterocyclic compound, 147754-12-9, name is 4-Fluoro-2-methylbenzonitrile, 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. Quality Control of 4-Fluoro-2-methylbenzonitrile

2-methyl-4-fluorophenyl-carbonitrile (2g, 14.8mM, 1.0equiv) in carbon tetrachloride (24mL) was added N- bromosuccinimide (2.64g, 14.8mM, 1.0equiv ), benzoyl peroxide (BPO, 179mg, 0.74mM, 0.05equiv), and heated to reflux for 3h under nitrogen. The reaction was complete by TLC, cooled to room temperature, filtered, washed with carbon tetrachloride, the solvent was concentrated under reduced pressure to give the crude product as a white solid. It was used directly in the next reaction without purification.

The synthetic route of 4-Fluoro-2-methylbenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu Bestchiralbio Limited-Liability Company; Li, Dequn; (16 pag.)CN105272963; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

147754-12-9, name is 4-Fluoro-2-methylbenzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of 4-Fluoro-2-methylbenzonitrile

In a dried reaction flask, 4-fluoro-2-methylbenzonitrile (4.055g, 30.0mmol) and hydrazine hydrate (85percent) (3.54mL, 60.0mmol) were dissolved in ethanol (15.9mL). In the protection from light and under the nitrogen atmosphere, the solution was heated under reflux at 80¡ãC for 48hr. Water was added to the reaction solution. The mixture was filtered. The filtered cake was rinsed with water to produce a pale yellow solid, which was suspended in ethyl ether. A hydrogen chloride gas was passed into the suspension under an ice-salt bath. The suspension was filtered. The filtered cake was rinsed with ethyl ether to produce an off-white solid (2.04g) in 37.0percent yield.

The synthetic route of 147754-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KBP Biosciences Co., Ltd.; HUANG, Zhenhua; WANG, Jinyuan; ZHANG, Dedong; EP2607363; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 147754-12-9, name is 4-Fluoro-2-methylbenzonitrile, 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. 147754-12-9

1.35 g 2-methyl-4-fluorobenzonitrile (10mmol) was dissolved in 20 mL of carbon tetrachloride, and 0.25g of p-toluene sulfonic acid (0.015 mmol) and 2.15g N-bromo succinimide (NBS) (12mmol) was added. The reaction was completed after heating for 4 hours, and then cooled to room temperature, filtered, and 20 mL saturated ammonium chloride solution was added and layers were obtained. The organic layer was washed with water and saturated sodium chloride aqueous solution (20 mL * 3) successively to clarification, dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure, and the obtained crude product was purified by column chromatography (petroleum ether: ethyl acetate = 3: 1) to obtain 2-bromomethyl-4-fluoro-benzonitrile (86percent yield). The 2-bromomethyl-4-fluorobenzonitrile (1.0 mmol) and p-toluidine (1.2mmol) was dissolved in 50 mL of tetrahydrofuran, stirred and heated to 60 ¡ã C under reflux, and was added 0.2g sodium ethoxide (3.0mmol) portionwise, and refluxed further 8 hours. After the reaction was confirmed complete by TLC monitoring, the reaction was cooled to room temperature, concentrated, and added 20 mL ethyl acetate, washed with water and saturated sodium chloride solution (20 mL * 3) successively to clarification, dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure to remove the solvent. The resulting crude product was purified by column chromatography (petroleum ether: ethyl acetate = 10: 1) to give the intermediate compound (1.1) 2-(p-methylphenylamino) methyl-4-fluoro-benzonitrile (95percent yield), mass spectrum (ESI +): m/z = 241.4 (M + H) +.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 147754-12-9.

Reference:
Patent; Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences; LI, Yanping; LI, Zhuorong; PENG, Zonggen; LI, Jianrui; JIANG, Xinbei; CHEN, Jinhua; JIANG, Jiandong; (30 pag.)EP3339287; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts