Methanol → Benzene, 1-bromo-3-(methylsulfonyl)-

HRID 380007Notes

Reaction equation

HRID 380007 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](SC)[CH:5]=[CH:6][CH:7]=1.O[O:11][S:12]([O-:14])=O.[K+].[CH3:16]O>O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([S:12]([CH3:16])(=[O:14])=[O:11])[CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 27356273-BromothioanisoleHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 2757146Benzene, 1-bromo-3-(methylsulfonyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3-Bromothioanisole was dissolved in methanol (20 ml) and cooled to 0° C. (ice/water bath). A solution of Oxone® (9.22 g) in water (30 ml) was added to this and the resultant cloudy slurry was stirred at room temperature for 3 hours. The reaction mixture was diluted with water and product extracted with dichloromethane. The combined fractions of dichloromethane were washed with brine and dried over anhydrous magnesium sulfate. After filtration, solvent was removed by evaporation under reduced pressure to give the sub-title compound as a solid (1.02 g).

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined fractions of dichloromethane were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration, solvent
  5. customwas removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-3090aeaf62e34a87881bfec50af3c287
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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