Chemical Properties
White to light yellow crystalline powder
Uses
As organic intermediate, pharmaceutical intermediate. In chemical synthesis.
Synthesis
The general procedure for the synthesis of 4-fluoro-2-methylbenzonitrile from 4-fluoro-2-methylbenzenemethanol was as follows: in a 25 mL Schlenk tube equipped with a magnetic stirrer, CuCl (0.05 mmol, 5 mol%), DABCO (0.10 mmol, 10 mol%) and 4-HO-TEMPO (0.05 mmol, 5 mol%). Subsequently, a solution of acetonitrile (2 mL) with 4-fluoro-2-methylbenzenemethanol (1 mmol) and an aqueous ammonia solution (25-28%, 3 mmol, 3.0 equiv) was added. The reaction mixture was stirred at room temperature under argon protection for 24 h. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate. The organic layers were combined and dried with anhydrous magnesium sulfate. Subsequently, the organic layer was concentrated under reduced pressure and the crude product was purified by column chromatography to afford the target product 4-fluoro-2-methylbenzonitrile.
References
[1] Organic Letters, 2013, vol. 15, # 8, p. 1850 - 1853
[2] Chinese Chemical Letters, 2018, vol. 29, # 3, p. 464 - 466
