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

Temperature

-20 °C

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.

1. additionAfter addition
2. stirringstirred at room temperature for 12 hours
3. additionwas added
4. stirringstirred for 0.5 hour
5. customthe organic phase was collected
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated
8. custompurified by column chromatography (silica gel, Petroleum ether/ethyl acetate=20:1)

ORD record

ord-c62d520e181b40859eb9c50a27c8502c

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206128B2