Dichloromethane → (4-Hydroxyphenyl)diphenylsulfonium chloride

HRID 992175Notes

Reaction equation

HRID 992175 reaction equation
C(Cl)[Cl:2].FC(F)(F)S([O-])(=O)=O.[C:12]1([S+:18]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:19]2[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.B(Br)(Br)Br.C(Cl)Cl>CO>[Cl-:2].[C:12]1([S+:18]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11619123(4-Methoxyphenyl)diphenylsulfonium triflateHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 18411308(4-Hydroxyphenyl)diphenylsulfonium chloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methylene chloride solution of 20 g of the diphenyl-4-methoxyphenylsulfonium trifluoromethanesulfonate, 90 ml of a 1 M boron tribromide-methylene chloride solution was slowly dropwise added with stirring at room temperature, and the mixture was stirred at room temperature for 2 hours. To the reaction mixture formed, methanol and distilled water were slowly added, followed by drying under reduced pressure to obtain a white crystal compound. The white crystal compound was dissolved in methanol, and ion exchange was effected using an anionic ion-exchange resin (Cl− type), followed by drying under reduced pressure to obtain 11.5 g of diphenyl-4-hydroxyphenylsulfonium chloride.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. customTo the reaction mixture formed
  3. distillationmethanol and distilled water
  4. additionwere slowly added
  5. customby drying under reduced pressure
  6. customto obtain a white crystal compound
  7. customby drying under reduced pressure

Sources & evidence

ORD record
ord-eaf75bf8c42643fe809aa8a81c396d20
Source dataset
uspto-grants-2002_10
Patent number
US06468714B2

Reaction notes

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