Dichloromethane → Triphenylsulfonium perfluorooctanesulfonate

HRID 1636833Notes

Reaction equation

HRID 1636833 reaction equation
[K+].[F:2][C:3]([F:30])([S:26]([O-:29])(=[O:28])=[O:27])[C:4]([F:25])([F:24])[C:5]([F:23])([F:22])[C:6]([F:21])([F:20])[C:7]([F:19])([F:18])[C:8]([F:17])([F:16])[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11].[Br-].[C:32]1([S+:38]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.ClCCl>O>[F:30][C:3]([F:2])([S:26]([O-:29])(=[O:28])=[O:27])[C:4]([F:24])([F:25])[C:5]([F:23])([F:22])[C:6]([F:20])([F:21])[C:7]([F:19])([F:18])[C:8]([F:17])([F:16])[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11].[C:45]1([S+:38]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 11984010Triphenylsulfonium BromideHCID 23669238Potassium perfluorooctanesulfonate

Product 1

HCID 21863781Triphenylsulfonium perfluorooctanesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of perfluorooctanesulfonic acid potassium salt (10.76 g, 20.0 mmol) in water (100 mL) at room temperature under nitrogen was added dropwise triphenylsulfonium bromide (6.87 g, 20.0 mmol) over 15 min. After stirring the suspension for 30 min., dichloromethane (100 mL) was added and the biphasic mixture stirred at room temperature for 20 h. Additional dichloromethane (100 mL) was added and the layers separated. The organic layer was washed with water (3×75 mL) until the washings were neutral (pH 7). After drying (MgSO4), removal of the solvent in vacuum gave a viscous gum which was further dried by heating at 50° C. for 24 h under vacuum. In this way, triphenylsulfonium perfluorooctanesulfonate was isolated as a pale yellow gummy solid.

Workup

  1. stirringthe biphasic mixture stirred at room temperature for 20 h
  2. customthe layers separated
  3. washThe organic layer was washed with water (3×75 mL) until the washings
  4. customAfter drying
  5. custom(MgSO4), removal of the solvent in vacuum
  6. customgave a viscous gum which
  7. customwas further dried

Sources & evidence

ORD record
ord-9caaa60e2cae44c0a9a73bde6e9a5cdb
Source dataset
uspto-grants-2000_03
Patent number
US06037107

Reaction notes

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