m-Chloroperbenzoic acid → 1-Bromo-3-methanesulfinylbenzene
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:18])C=1>CCOC(C)=O.O>[CH3:9][S:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)=[O:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 3-bromothioanisole (4.9687 g, 0.0245 mmol) and MCPBA (5.066 g, %) was stirred at room temperature. After 4 h, extractive EtOAc/H2O workup followed by flash chromatography (EtOAc/Hexanes, 50:50) provided the title compound (3.725 g, 69%) as an oil. 1H NMR (DMSO, 400 MHz): 7.80 (br s, 1H), 7.61 (d, J=8.01 Hz, 1H), 7.53 (d, J=8.01 Hz, 1H), 7.39 (t, J=8.01 Hz, 1H), 2.72 (s, 3H).
Sources & evidence
- ORD record
- ord-11316bbd519e455487b1dd378029690e
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07329668B2
Reaction notes
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