3-Chloro-4-trifluoromethylphenol

Preparation 53-Chloro-4-(trifluoromethyl)phenolTo a stirred sol ution 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, 60percent 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 x 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, 72percent).To a solution of (2-(3-chloro-4-(trifluoromethyl)phenoxy)ethyl)trimethylsilane (Preparation 15, 3.1 g, 10 mmol) in 1, 4-dioxane (5 mL) was added tetrabutylammonium fluoride (10 mL, 1M in THF) and the resulting mixture was stirred at room temperature for 18 hours under nitrogen. The mixture was poured onto water and neutralised with aq. ammonium chloride and extracted with ethyl acetate (3.x.30 mL). The organic layer was separated and washed with 1M sodium hydroxide (3.x.30 mL). The aqueous layers were separated, combined, acidified with aqueous 2M HCl and re-extracted with ethyl acetate (3.x.30 mL), dried (MgSOTo a sulfuric acid (14 ml) -HA mixture of To a solution of