2-(Trimethylsilyl)ethanol → 3-Chloro-4-(trifluoromethyl)phenol

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a stirred solution of 2-chloro-4-fluorobenzotrifluoride (500 mg, 2.52 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added 2-(trimethylsilyl)ethanol (0.40 mL, 2.77 mmol) and the reaction mixture was cooled to 0° C. Sodium hydride (302 mg, 60% w/w dispersion in oil, 7.55 mmol) was then added portionwise. After 5 minutes a thick white suspension had formed. The reaction mixture was warmed to room temperature slowly and then stirred for a further 16 hours. The reaction mixture was then quenched with ice water (50 mL) and washed with diethyl ether (50 mL). The aqueous extracts were acidified with aqueous 2 M hydrogen chloride solution and extracted with diethyl ether (2×50 mL). The organic extracts were dried over anhydrous magnesium sulphate and evaporated in vacuo for 16 hours to afford the title compound as a yellow oil (356 mg, 72%).

Herkunft & Nachweise