Water → 1-Bromo-4-trifluoromethanesulfonylbenzene

HRID 1057161Notes

Reaction equation

HRID 1057161 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[OH:13]S(O)(=O)=O.[OH2:18]>[O-2].[O-2].[O-2].[Cr+6]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:9]([F:12])([F:10])[F:11])(=[O:13])=[O:18])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 7364134-(Trifluoromethylthio)bromobenzene

Product 1

HCID 3001141-Bromo-4-trifluoromethanesulfonylbenzene

Reagents, catalysts & solvents 1

HCID 10219390chromium (VI) trioxideCatalyst

Procedure

Chromium trioxide (1.2 g, 11.7 mmol) was added to a solution of (4-bromophenyl)(trifluoromethyl)sulfane (1.5 g, 5.83 mmol), concentrated H2SO4 (6 mL), and H2O (10 mL). After stirring at rt for 2 h, the reaction mixture was poured into ice-water and extracted with EtOAc (3×60 mL). The combined organic layers were dried (MgSO4), concentrated, and purified by column chromatography on silica gel (EtOAc/petroleum ether=1:100) to give 960 mg of 1-bromo-4-((trifluoromethyl)sulfonyl)benzene as a white solid. 1H NMR (CDCl3, 400 MHz): δ 7.89 (d, 2H), 7.85-7.81 (m, 2H). 13C NMR (CDCl3, 100 MHz): δ 133.4, 132.8, 132.1, 130.4, 119.7 (q, J=320 Hz).

Workup

  1. extractionextracted with EtOAc (3×60 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by column chromatography on silica gel (EtOAc/petroleum ether=1:100)

Sources & evidence

ORD record
ord-f979a2f71f814b25beb74f3ccee6ba4d
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

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