Methanol → (R)-1-(4-Bromophenyl)ethanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(4-bromophenyl)ethanone (5.0 g, 25 mmol) and (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole (1.25 mL, 1 M) in 80 mL of anhydrous dichloromethane was added Borane-methyl sulfide complex (2.1 g, 27 mmol) over 1 hour at −200C. After addition completed, the mixture was stirred at −20° C. for 2 hours, then stirred at room temperature for 12 hours. After the reaction, 20 mL of methanol was added, and stirred for 0.5 hour. Then the mixture was diluted with 100 mL of water and the organic phase was collected, dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (silica gel, Petroleum ether/ethyl acetate=20:1) to give (R)-1-(4-bromophenyl)ethanol (4.6 g, 92%) as the white solid.

Provenance & Evidence