Diphenyl sulfoxide → Triphenylsulfonium Bromide

HRID 584041Notes

Reaction equation

HRID 584041 reaction equation
[C:1]1([S:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-:15].[Al+3].[Br-].[Br-]>C1C=CC=CC=1>[Br-:15].[C:1]1([S+:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 13679Diphenyl sulfoxideHCID 166749Bromhydrol

Product 1

HCID 11984010Triphenylsulfonium BromideYield 128.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 200 ml of benzene were dissolved 21.1 g (0.1 mol) of diphenylsulfoxide, and 160.0 g (0.6 mol) of aluminum bromide at room temperature were added thereto, followed by allowing to react at 80° C. for 2 hours with stirring. The reaction solution was poured into 1000 ml of ice and extracted 3 times with methylene chloride. Thus obtained organic layer was dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure to give 22.0 g (yield: 64%) of triphenylsulfonium bromide as a white crystal.

Workup

  1. additionwere added
  2. customto react at 80° C. for 2 hours
  3. extractionextracted 3 times with methylene chloride
  4. dry with materialThus obtained organic layer was dried over anhydrous magnesium sulfate
  5. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-cf2c1b4f48284176a14681a74edf5a2c
Source dataset
uspto-grants-2005_08
Patent number
US06924323B2

Reaction notes

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