Toluene → (4-Methylphenyl)(diphenyl)sulfanium trifluoromethanesulfonate

HRID 1873107Notes

Reaction equation

HRID 1873107 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.[C:15]1([CH3:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[S:22]([O:29]S(C(F)(F)F)(=O)=O)([C:25]([F:28])([F:27])[F:26])(=[O:24])=[O:23]>ClCCl.CCOCC>[O-:29][S:22]([C:25]([F:28])([F:27])[F:26])(=[O:24])=[O:23].[C:9]1([S+:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:18]2[CH:19]=[CH:20][C:15]([CH3:21])=[CH:16][CH:17]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 13679Diphenyl sulfoxideHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 16213832(4-Methylphenyl)(diphenyl)sulfanium trifluoromethanesulfonateYield 95.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

Both 1 g of phenyl sulfoxide and 0.51 g of toluene dissolved in 50 mL dichloromethane was stirred and then, 1.48 g of triflic anhydride was slowly added to the mixture. The reacting mixture was stirred at the same temperature for 30 minutes, and the reaction temperature was slowly increased up to room temperature. Then, the reacting mixture was washed with distilled water. After the complete removal of organic solvent contained in the washed organic layer under vacuum drying, an oil phase with larger viscosity was obtained. The oil phase, so formed, was completely dissolved in dichloromethane and with a slow addition of ether, a white precipitate was obtained. The precipitate was filtered, and dried by vaccum oven to obtain 2.01 g of diphenyl(4-methyl phenyl)sulfonium triflate (yield: 94%) in a white solid. The formula was shown in the table 1.

Workup

  1. stirringThe reacting mixture was stirred at the same temperature for 30 minutes
  2. washThen, the reacting mixture was washed with distilled water
  3. customAfter the complete removal of organic solvent
  4. customdrying
  5. customan oil phase with larger viscosity was obtained
  6. customThe oil phase, so formed
  7. customa white precipitate was obtained
  8. filtrationThe precipitate was filtered
  9. customdried by vaccum oven

Sources & evidence

ORD record
ord-81c210801e1e45d58ba4ce8be3333e31
Source dataset
uspto-grants-2000_08
Patent number
US06111143

Reaction notes

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