Methanol → 5-Bromo-1,3-difluoro-2-(methanesulfonyl)benzene

HRID 748944Notes

Reaction equation

HRID 748944 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5](SC)=[C:6]([F: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]([F:8])[C:5]([S:14]([CH3:18])(=[O:16])=[O:13])=[C:4]([F:11])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 235966125-Bromo-1,3-difluoro-2-(methylsulfanyl)benzeneHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 685147935-Bromo-1,3-difluoro-2-(methanesulfonyl)benzeneYield 40%

Procedure

Combine 5-bromo-1,3-difluoro-2-methylsulfanyl-benzene (1.1 g, 4.6 mmol), oxone (11 g, 18.4 mmol) and methanol (20 mL). Stir for 12 hours. Filter the suspension and evaporate the filtrate. Dissolve the residue in dichloromethane (100 mL) and add water (100 mL). Separate the organic layer and wash with brine (50 mL). Dry with MgSO4, filter and concentrate in vacuo. Chromatograph the residue on a column eluting the material with diethyl ether in hexane (0 to 5%) to give 497 mg of the title compound (40%).

Workup

  1. filtrationFilter the suspension
  2. customevaporate the filtrate
  3. dissolutionDissolve the residue in dichloromethane (100 mL)
  4. additionadd water (100 mL)
  5. customSeparate the organic layer
  6. washwash with brine (50 mL)
  7. dry with materialDry with MgSO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo
  10. washChromatograph the residue on a column eluting the material with diethyl ether in hexane (0 to 5%)

Sources & evidence

ORD record
ord-95e44c5987ad40c19ff36aa9db16eba0
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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