Hydrogen Bromide → 2-Bromo-1-(2-fluorophenyl)-2-(phenylthio)ethanone
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:17])[CH2:9][S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[BrH:18]>C(OCC)(=O)C.C(O)(=O)C.[Cu](Br)Br>[Br:18][CH:9]([S:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])=[O:17]Participants
6
Procedure
To a solution of 1-(2-fluorophenyl)-2-(phenylthio)ethanone (413 mg) in ethyl acetate (6 mL) were added copper (II) bromide (419 mg) and a 47% solution (2 drops) of hydrogen bromide in acetic acid and the mixture was stirred at 80° C. for 2 hr. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound as a brown oil (yield 503 mg, yield 92%).
Workup
- concentrationconcentrated under reduced pressure
- additionA saturated aqueous sodium hydrogen carbonate solution was added to the residue
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-e0323f0406d444b8bd7ec443a8e870be
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08334301B2
Reaction notes
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