Sodium borohydride → (5-Bromo-2-chloro-phenyl)-[4-(trifluoromethoxy)phenyl]methanol

Participants

Reaction Conditions

Reaction Steps

(5-bromo-2-chloro-phenyl)-[4-(trifluoromethoxy)phenyl]methanone 6f (4.35 g, 11.5 mmol) was dissolved in 40 mL of mixed solution (THF and MeOH, v:v=1:1) and cooled to 0° C., followed by addition of sodium borohydride (0.87 g, 23.0 mmol) in batch. The reaction mixture was stirred for 30 minutes at 0° C. Thereafter, the reaction mixture was concentrated under reduced pressure after 10 mL acetone were added. The reaction mixture was partitioned after 100 mL ethyl acetate and 50 mL water were added and the organic extract was washed with saturated sodium chloride solution (50 mL×2), combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (5-bromo-2-chloro-phenyl)-[4-(trifluoromethoxy)phenyl]methanol 6g (4.4 g, pale yellow grease), which was used directly in the next step without purification. 1H NMR (400 MHz, CDCl3): δ 7.80 (d, 1H), 7.43-7.40 (m, 2H), 7.36 (dd, 1H), 7.20 (t, 3H), 6.16 (s, 1H).

Provenance & Evidence