Methanol → 5-Bromo-2-methanesulfonyl-1,3-dimethyl-benzene

HRID 732834Notes

Reaction equation

HRID 732834 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:11])[C:5](SC)=[C:6]([CH3:8])[CH:7]=1.O[O:13][S:14]([O-:16])=O.[K+].[CH3:18]O>>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:14]([CH3:18])(=[O:16])=[O:13])=[C:4]([CH3:11])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 685195015-Bromo-1,3-dimethyl-2-(methylsulfanyl)benzene

Product 1

HCID 685159425-Bromo-2-methanesulfonyl-1,3-dimethyl-benzeneYield 50%

Procedure

Dissolve 5-bromo-1,3-dimethyl-2-methylsulfanyl-benzene (555 mg, 2.42 mmol) in methanol (30 mL) and treat with oxone (6.0 g, 9.8 mmol). Stir the mixture at ambient temperature for 1 hour. Filter the suspension through silica gel and elute with CH2Cl2 (100 mL). Evaporate the filtrate to give 316 mg (50%) of the title compound.

Workup

  1. filtrationFilter the suspension through silica gel
  2. washelute with CH2Cl2 (100 mL)
  3. customEvaporate the filtrate

Sources & evidence

ORD record
ord-45eb8a536d4d4b6eb4f628bbc4618e08
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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