2-Bromo-4-cyanobenzyl alcohol

89891-69-0

90110-98-8

General procedure for the synthesis of 3-bromo-4-(hydroxymethyl)benzonitrile from 3-bromo-4-formylbenzonitrile: 3-bromo-4-formylbenzonitrile (1.0 g, 4.8 mmol) was dissolved in methanol (30 mL) and the solution was cooled to 0 °C. Sodium borohydride (180 mg, 4.8 mmol) was added in batches under stirring. When the addition was complete, the reaction mixture was slowly warmed to room temperature and stirring was continued at this temperature for 1 hour. Upon completion of the reaction, the reaction was quenched with 1N hydrochloric acid solution, followed by concentration under reduced pressure to remove the solvent. The residue was extracted with ethyl acetate (25 mL x 3). The organic phases were combined, washed with saturated saline (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target product 3-bromo-4-(hydroxymethyl)benzonitrile as a white solid (1.0 g, 99% yield). The structure of the product was confirmed by NMR hydrogen spectroscopy (300 MHz, CDCl3) and liquid chromatography-mass spectrometry (LC-MS): 1H NMR (300 MHz, CDCl3) δ 7.82 (s, 1H), 7.49-7.71 (m, 2H), 4.75 (s, 2H); LC-MS m/z 212 [M+1]+.