Benzene → Diphenyl(trifluoromethyl)sulfanium trifluoromethanesulfonate

HRID 1019335Notes

Reaction equation

HRID 1019335 reaction equation
[F:1][C:2]([S:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O)([F:4])[F:3].[CH:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[S:19]([O:26]S(C(F)(F)F)(=O)=O)([C:22]([F:25])([F:24])[F:23])(=[O:21])=[O:20]>>[O-:26][S:19]([C:22]([F:25])([F:24])[F:23])(=[O:21])=[O:20].[C:7]1([S+:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:2]([F:4])([F:3])[F:1])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 67749Trifluoromethanesulfonic anhydrideHCID 9794162PHENYL TRIFLUOROMETHYL SULFOXIDE

Product 1

HCID 18401167Diphenyl(trifluoromethyl)sulfanium trifluoromethanesulfonateYield 40%

Conditions

Temperature
0 °C

Procedure

Phenyl trifluoromethyl sulfoxide (0.4 g, 2.1 mmol) and then benzene (4.9 g, 64 mmol) are introduced, under an inert atmosphere and at approximately 0° C. (lower limit below which benzene crystallizes), into a Schlenck tube purged beforehand with argon. Five equivalents of triflic anhydride (2.82 g, 10 mmol) are gradually added. The mixture is stirred for 1 h at 0° C. and then for 24 h at ambient temperature. The medium is evaporated and the residue is purified by chromatography with the CH3CN/CH2Cl2 (1/4) mixture as eluent. White crystals, having a melting point of 69-70° C., are obtained with a yield of 40%.

Workup

  1. custom(lower limit below which benzene crystallizes)
  2. custominto a Schlenck tube purged beforehand with argon
  3. waitfor 24 h at ambient temperature
  4. customThe medium is evaporated
  5. customthe residue is purified by chromatography with the CH3CN/CH2Cl2 (1/4) mixture as eluent
  6. customare obtained with a yield of 40%

Sources & evidence

ORD record
ord-bd50ede838ce4c17a8937c6bff89bbea
Source dataset
uspto-grants-2002_11
Patent number
US06486351B1

Reaction notes

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