Water → 1-Bromo-3-(ethanesulfonyl)benzene

HRID 1962766Notes

Reaction equation

HRID 1962766 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]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 130827271-Bromo-3-(ethylsulfanyl)benzene

Product 1

HCID 574779081-Bromo-3-(ethanesulfonyl)benzeneYield 92%

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): 8.09 (m, 1H), 7.85 (d, 1H), 7.78 (d, 1H) 7.45 (t, 1H), 3.14 (q, 2H), 1.25 (t, 3H).

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialThe combined organic layers were dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude residue was purified by flash column chromatography with a hexane

Sources & evidence

ORD record
ord-665059f8a9e747fdb372aebdd793eba2
Source dataset
uspto-grants-2013_04
Patent number
US08415362B2

Reaction notes

Loading…