Sodium Sulfite → 1-Bromo-4-methanesulfonyl-2-methylbenzene

HRID 422556Notes

Reaction equation

HRID 422556 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](SC)=[CH:4][C:3]=1[CH3:10].O[O:12][S:13]([O-:15])=O.[K+].S([O-])([O-])=O.[Na+].[Na+].[CH3:23]O.O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:13]([CH3:23])(=[O:15])=[O:12])=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 4

HCID 24437Sodium SulfiteHCID 22242641Methanol--water (1/1)HCID 23707502Potassium hydroxy sulfiteHCID 26370189(4-Bromo-3-methylphenyl)(methyl)sulfane

Product 1

HCID 593508361-Bromo-4-methanesulfonyl-2-methylbenzene

Procedure

To a heterogenous solution of (4-bromo-3-methylphenyl)(methyl)sulfane (2.17 g, 9.99 mmol) in 55 mL of 10/1 MeOH/water at 0° C. was added oxone (6.14 g, 9.99 mmol). The solution was allowed to warm up to RT and stirred overnight. Saturated sodium sulfite (aq.) was added and the mixture was extracted with DCM (3×). The combined organic layers were washed with water and NaCl (sat.), dried over sodium sulfate, filtered and concentrated to afford 2.30 g of 1-bromo-2-methyl-4-(methylsulfonyl)benzene 2.30 g as a white solid.

Workup

  1. extractionthe mixture was extracted with DCM (3×)
  2. washThe combined organic layers were washed with water and NaCl (sat.)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0de6490dabce407d8fdfb8f1625d909a
Source dataset
uspto-grants-2012_01
Patent number
US08101612B2

Reaction notes

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