Water → 4-Bromo-1-(methylsulfonyl)-2-(trifluoromethyl)benzene

HRID 732765Notes

Reaction equation

HRID 732765 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:22])C=1.[OH2:25]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:9])(=[O:22])=[O:25])=[C:4]([C:10]([F:13])([F:11])[F:12])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 223153184-Bromo-1-(methylthio)-2-(trifluoromethyl)-benzene

Product 1

HCID 223152224-Bromo-1-(methylsulfonyl)-2-(trifluoromethyl)benzeneYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine 4-bromo-1-methylsulfanyl-2-trifluoromethyl-benzene (3.6 g, 15 mmol), mCPBA (7.7 g, 30 mmol) and dichloromethane (100 mL). Stir for 2 hours. Dilute with dichloromethane (300 mL) and water (100 mL). Separate the organic layer and wash with aqueous saturated NaHCO3 (2×100 mL) and brine (100 mL). Dry with MgSO4, filter and concentrate in vacuo. Wash the solid with diethyl ether (2×10 mL) and dichloromethane (10 mL) to give 2.06 g of the title compound (44%).

Workup

  1. customSeparate the organic layer
  2. washwash with aqueous saturated NaHCO3 (2×100 mL) and brine (100 mL)
  3. dry with materialDry with MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. washWash the solid with diethyl ether (2×10 mL) and dichloromethane (10 mL)

Sources & evidence

ORD record
ord-d6772063f0844fdaa1cc4834d23ab77d
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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