Dimethyl Sulfide → (R)-1-bromo-1-[3,5-bis(trifluoromethyl)phenyl]ethane

Under an argon atmosphere, a suspension of N-bromosuccinimide (206 mg, 1.16 mmol) in anhydrous dichloromethane (3.8 mL) was added dropwise with dimethyl sulfide (105 μL, 1.40 mmol) under ice cooling over 3 minutes. The mixture was added dropwise with a solution of (S)-1-[3,5-bis(trifluoromethyl)phenyl]ethanol (200 mg, 0.78 mmol, >99.5% ee) in anhydrous dichloromethane (2 mL) at −20° C., and the mixture was stirred at room temperature for 9 hours. The reaction mixture was add with n-hexane, and the organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent, n-hexane) to obtain 144 mg of (R)-1-bromo-1-[3,5-bis(trifluoromethyl)phenyl]ethane as colorless oil.

1. washthe organic layer was washed with water and saturated brine
2. dry with materialdried over anhydrous sodium sulfate
3. concentrationconcentrated under reduced pressure
4. customThe resulting residue was purified by silica gel column chromatography (developing solvent, n-hexane)

ORD record

ord-784360cb722e4a98a76c64186e1e102e

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09272966B2