Tetrahydrofuran → 2-Bromo-4-(isopropylsulfonyl)-1-methylbenzene

HRID 2390161Notes

Reaction equation

HRID 2390161 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](SC(C)C)[CH:5]=[CH:4][C:3]=1[CH3:12].O[O:14][S:15]([O-:17])=O.[K+].[CH2:19]1[CH2:23]OC[CH2:20]1>O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([S:15]([CH:19]([CH3:23])[CH3:20])(=[O:17])=[O:14])[CH:5]=[CH:4][C:3]=1[CH3:12]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 585218832-Bromo-4-(isopropylthio)-1-methylbenzene

Product 1

HCID 585220592-Bromo-4-(isopropylsulfonyl)-1-methylbenzeneYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A cooled (0° C.) solution of 2-bromo-4-(isopropylthio)-1-methylbenzene (123 mg) in THF (10 ml) was treated with a solution of oxone (580 mg) in water (6 ml). The reaction mixture was stirred at RT for 16 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over sodium sulfate and concentrated to give the title compound (120 mg, 92%).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2cddf8cfcee24c709daf6588306fcb07
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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