Methanol → 1-(Bromomethyl)-2-methanesulfonylbenzene

HRID 1290014Notes

Reaction equation

HRID 1290014 reaction equation
CS[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][Br:6].O[O:12][S:13]([O-:15])=O.[K+].[CH3:17]O>O>[CH3:17][S:13]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][Br:6])(=[O:15])=[O:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 217935191-(Bromomethyl)-2-(methylsulfanyl)benzeneHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 189224741-(Bromomethyl)-2-methanesulfonylbenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 124 mg (0.57 mmol) of 2-(methylthio)-benzylbromide in 8.0 mL of methanol was added a solution of 702 mg of oxone in 7.0 mL of water. The solution was stirred for 4.5 h, concentrated in vacuo and purified by silica gel flash chromatography, eluting with 10% ethyl acetate/hexane to give 105 mg of the title compound. mass spec 249(M+). NMR (CDCl3): δ 3.25 (s, 3H), 5.07 (s, 2H), 7.50 (m, 1H), 7.60 (m, 2H), 8.05 (d, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by silica gel flash chromatography
  3. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-11363b0229f34597bd9f6f342ba64980
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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