Dichloromethane → Triphenylsulfonium perfluorooctanesulfonate

HRID 890575Notes

Reaction equation

HRID 890575 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-189c2bb10ac24f4eb6b1b87233954f89
Source dataset
uspto-grants-2006_02
Patent number
USRE038980E1

Reaction notes

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