Diphenyl sulfide → Sulfonium, triphenyl-, 1,1,1-trifluoromethanesulfonate (1:1)

HRID 2232045Notes

Reaction equation

HRID 2232045 reaction equation
[O-:1][S:2]([C:5]([F:8])([F:7])[F:6])(=[O:4])=[O:3].C1([I+][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)C=CC=CC=1.[C:22]1([S:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C([O-])(=O)C1C=CC=CC=1.[Cu+2].C([O-])(=O)C1C=CC=CC=1>[O-:4][S:2]([C:5]([F:8])([F:7])[F:6])(=[O:3])=[O:1].[C:29]1([S+:28]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 8766Diphenyl sulfideHCID 2737137Diphenyliodonium trifluoromethanesulfonate

Product 1

HCID 11729320Sulfonium, triphenyl-, 1,1,1-trifluoromethanesulfonate (1:1)

Reagents, catalysts & solvents 1

HCID 164650Cupric benzoateCatalyst

Conditions

Temperature
125 °C

Procedure

A flask was charged with 2.0 g (4.8 mmol) of diphenyliodonium triflate, 0.93 g (5.0 mmol) diphenyl sulfide and 37 mg of copper benzoate. The mixture was heated under argon for 3 h (bath 125° C.). After cooling, the mixture was triturated with hot ether and stirred 1 h. The solid was filtered and recrystallized from 1:1 butyl acetate-isopropanol (1.6 g, 80%, mp 134°-6° C.).

Workup

  1. temperatureAfter cooling
  2. customthe mixture was triturated with hot ether
  3. filtrationThe solid was filtered
  4. customrecrystallized from 1:1 butyl acetate-isopropanol (1.6 g, 80%, mp 134°-6° C.)

Sources & evidence

ORD record
ord-c16fb5d0325d4544b2589b238e8ce1b0
Source dataset
uspto-grants-1988_11
Patent number
US04786441

Reaction notes

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