m-Chloroperbenzoic acid → Benzene, 1-bromo-4-[(trifluoromethyl)sulfinyl]-

HRID 1057162Notes

Reaction equation

HRID 1057162 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1>ClCCl>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([S:19]([C:20]([F:23])([F:21])[F:22])=[O:9])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 7364134-(Trifluoromethylthio)bromobenzene

Product 1

HCID 19384253Benzene, 1-bromo-4-[(trifluoromethyl)sulfinyl]-Yield 47.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Meta-Chloroperbenzoic acid (1.2 g, 11.7 mmol) was added to a solution of (4-bromophenyl)(trifluoromethyl)sulfane (1.7 g, 6.61 mmol) in dichloromethane (30 mL). After stirring at rt for 12 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=0:100 to 1:50) to give 859 mg of 1-bromo-4-((trifluoromethyl)sulfinyl)benzene as a white solid. 1H NMR (CDCl3, 400 MHz): δ 7.79-7.75 (m, 2H), 7.66 (d, 2H). 13C NMR (CDCl3, 100 MHz): δ 134.8, 133.0, 128.7, 127.4, 124.4 (q, J=330 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=0:100 to 1:50)

Sources & evidence

ORD record
ord-6a59397602a5448b8ddca33286dfb429
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

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