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

Temperature

-20 °C

To a solution of 4-bromoacetophenone (5.0 g, 25 mmol) and (S)-2-Methyl-CBS-oxazaborolidine (1.25 mL, 1 M) in anhydrous dichloromethane (80 mL) was added borane-methyl sulfide complex (2.1 g, 27 mmol) over 1 hour at −20° C. After addition completed, the mixture was stirred at −20° C. for 2 hours, then stirred at room temperature for 12 hours. After the reaction, methanol (20 mL) was added, and stirred for 0.5 hour. Then the mixture was diluted with water (100 mL) and the organic phase was dried over anhydrous sodium sulfate. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:8) to give pure product (R)-1-(4-bromophenyl)ethanol as a white solid (4.6 g, 92%).

1. additionAfter addition
2. stirringstirred at room temperature for 12 hours
3. additionwas added
4. stirringstirred for 0.5 hour
5. dry with materialthe organic phase was dried over anhydrous sodium sulfate
6. filtrationThe mixture was filtered
7. concentrationthe filtrate was concentrated
8. customThe residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:8)

ORD record

ord-18c5057a1ad64e08b9f1d921a11a57aa

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206128B2