Dichloromethane → 2-Bromophenylmethylsulfoxide

HRID 1420839Notes

Reaction equation

HRID 1420839 reaction equation
[OH:1]OS([O-])=O.[K+].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14][CH3:15].C(=O)(O)[O-].[Na+].ClCCl>O.CC(C)=O>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([CH3:15])=[O:1]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 881662-BromothioanisoleHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 110748732-BromophenylmethylsulfoxideYield 113.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

Oxone (9.7 g) in water (40 ml) was added slowly to a stirred, cooled cooled (0° C.) solution of 2-bromothioanisole (5 g, 24.6 mmol) and sodium bicarbonate (16 g) in acetone (20 ml). The mixture was stirred for at room temperature 16 h., then water and dichloromethane was added. The layers were separated and the organic phase was dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with hexane/EtOAc (80:20 increasing to 40:60) to give the title compound (6.1 g). m/z (ES+) 219 (M+1).

Workup

  1. temperaturecooled
  2. customThe layers were separated
  3. dry with materialthe organic phase was dried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel
  6. washeluting with hexane/EtOAc (80:20 increasing to 40:60)

Sources & evidence

ORD record
ord-05da3fab12bc48b6b6030ec94b6d3426
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

Loading…