37900-81-5

94444-58-3

37900-81-5

The general procedure for the synthesis of 3-chloro-4-trifluoromethylphenol from 2-chloro-4-fluorobenzotrifluoride was as follows: to a stirred solution of 2-chloro-4-fluorobenzotrifluoride (500 mg, 2.52 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added 2-(trimethylmethylsilyl)ethanol (0.40 mL, 2.77 mmol), and the reaction mixture was cooled to 0 °C. Subsequently, sodium hydride (302 mg, 60% w/w oil dispersion, 7.55 mmol) was added in batches. after 5 min, the reaction mixture formed a thick white suspension. The reaction mixture was slowly warmed to room temperature and stirring was continued for 16 hr. Upon completion of the reaction, the reaction was quenched with ice water (50 mL) and washed with ether (50 mL). The aqueous phase was acidified with 2 M aqueous hydrochloric acid and subsequently extracted with ether (2 x 50 mL). The organic phases were combined, dried with anhydrous magnesium sulfate and concentrated in vacuum for 16 h to give 3-chloro-4-trifluoromethylphenol as a yellow oil (356 mg, 72% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 6.75 (dd, 1H), 6.95 (d, 1H), 7.51 (d, 1H).LCMS analysis showed a retention time of Rt = 1.23 min and a mass spectrum m/z 195 [MH]-.