Water → 1-Bromo-3-(ethanesulfonyl)benzene
Reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19][CH2:20][CH3:21])[CH:14]=1.C(Cl)Cl.[OH2:25]>>[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([CH2:20][CH3:21])(=[O:9])=[O:25])[CH:14]=1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
The MCPBA (2.37 g, 10.6 mmol) was added to a solution of 1-bromo-3-(ethylthio)benzene (1.00 g, 4.80 mmol) in DCM (10 ml, 156 mmol) cooled to 0° C. The reaction was stirred for 1 h and then was diluted with water and extracted with ethyl acetate three times. The combined organic layers were dried with magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude residue was purified by flash column chromatography with a hexane:ethyl acetate gradient to give 1-bromo-3-(ethylsulfonyl)benzene as a colorless oil 1.1 gm 92%, 1H NMR (300 MHz, CDCl3): δ8.09 (m, 1H), 7.85 (d, 1H), 7.78 (d, 1H) 7.45 (t, 1H), 3.14 (q, 2H), 1.25 (t, 3H).
Workup
- extractionextracted with ethyl acetate three times
- dry with materialThe combined organic layers were dried with magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe resulting crude residue was purified by flash column chromatography with a hexane
Sources & evidence
- ORD record
- ord-61c9fb86d3a34a55b6af165ac456a6bc
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541425B2
Reaction notes
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