Benzene → Pentafluoroethylphenyliodonium trifluoromethanesulfonate

HRID 1758178Notes

Reaction equation

HRID 1758178 reaction equation
FC(F)(F)C(O[I:6](OC(=O)C(F)(F)F)[C:7]([F:13])([F:12])[C:8]([F:11])([F:10])[F:9])=O.FC(F)(F)C(O)=O.[F:30][C:31]([F:37])([F:36])[S:32]([OH:35])(=[O:34])=[O:33].[CH:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[F:30][C:31]([F:37])([F:36])[S:32]([O-:35])(=[O:34])=[O:33].[F:13][C:7]([I+:6][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([F:12])[C:8]([F:9])([F:10])[F:11]

Participants

5

Reactant 4

HCID 241BenzeneHCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 12918315Di(trifluoroacetoxy)iodopentafluoroethane

Product 1

HCID 11488264Pentafluoroethylphenyliodonium trifluoromethanesulfonateYield 55%

Procedure

To a mixture of 6.05 g of di(trifluoroacetoxy)iodopentafluoroethane and 45 ml of trifluoroacetic acid was added 1.1 ml of trifluoromethanesulfonic acid while cooling in an ice bath and stirring, and thereafter 1.2 ml of benzene was added dropwise to the mixture. After completion of the addition, the mixture was stirred for 4.5 hours and the solvent was distilled off to obtain a crystalline solid which was then recrystallized from chloroform to obtain 3.32 g (55% yield) of pentafluoroethylphenyliodonium trifluoromethanesulfonate as colorless flake crystals.

Workup

  1. temperaturewhile cooling in an ice bath
  2. additionAfter completion of the addition
  3. stirringthe mixture was stirred for 4.5 hours
  4. distillationthe solvent was distilled off
  5. customto obtain a crystalline solid which
  6. customwas then recrystallized from chloroform

Sources & evidence

ORD record
ord-842397bac90f4877b043bf382ac07e32
Source dataset
uspto-grants-1983_02
Patent number
US04371710

Reaction notes

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