Dimethyl Sulfide → (S)-1-(1-bromoethyl)-3,5-bis(trifluoromethyl)benzene
Reaction equation
[Br:1]N1C(=O)CCC1=O.CSC.[F:12][C:13]([F:28])([F:27])[C:14]1[CH:15]=[C:16]([C@H:24](O)[CH3:25])[CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1.CCCCCC>ClCCl>[Br:1][C@H:24]([C:16]1[CH:15]=[C:14]([C:13]([F:28])([F:27])[F:12])[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=1)[CH3:25]Participants
Procedure
Under an argon atmosphere, a suspension of N-bromosuccinimide (103 mg, 0.58 mmol) in anhydrous dichloromethane (2.0 mL) was added dropwise with dimethyl sulfide (53 μL, 0.70 mmol) under ice cooling over 3 minutes. The mixture was added dropwise with a solution of (R)-1-[3,5-bis(trifluoromethyl)phenyl]ethanol (100 mg, 0.39 mmol, >99.5% ee) in anhydrous dichloromethane (1 mL) at −20° C., and the mixture was stirred at room temperature for 6 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 82 mg of (S)-1-bromo-1-[3,5-bis(trifluoromethyl)phenyl]ethane as colorless oil.
Workup
- washthe organic layer was washed with water and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (developing solvent, n-hexane)
Sources & evidence
- ORD record
- ord-95a292d379cf49a9a8287aa52a8348a5
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09272966B2
Reaction notes
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