Dichloromethane → Triphenylsulfonium perfluorooctanesulfonate

HRID 2913

Reaction equation

HRID 2913 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].[Cl-].[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 61343Triphenylsulfonium chlorideHCID 23669238Potassium perfluorooctanesulfonate

Product 1

HCID 21863781Triphenylsulfonium perfluorooctanesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of perfluorooctanesulfonic acid potassium salt (24.64 g, 46.1 mmol) in water (150 ml) at room temperature under nitrogen was added dropwise triphenylsulfonium chloride (50% aqueous solution, 27.50 g) over 15 minutes. After stirring the suspension for 30 minutes, dichloromethane (75 ml) was added and the mixture stirred at room temperature for 20 hours. Additional dichloromethane (225 ml) was added and the layers separated. The organic layer was washed with water (5×125 ml) until the washings were neutral (pH 7 ). After drying (MgSO4 ), removal of the solvent in vacuo gave a viscous gum which was further dried by heating at 80°-90° C. for 84 hours under vacuum. In this way, triphenylsulfonium perfluorooctanesulfonate was isolated as a glassy solid (30.61 g).

Workup

  1. stirringthe mixture stirred at room temperature for 20 hours
  2. customthe layers separated
  3. washThe organic layer was washed with water (5×125 ml) until the washings
  4. customAfter drying
  5. custom(MgSO4 ), removal of the solvent in vacuo
  6. customgave a viscous gum which
  7. customwas further dried
  8. temperatureby heating at 80°-90° C. for 84 hours under vacuum

Sources & evidence

ORD record
ord-d1e6e90adf2744bfa6b435f6c7114ace
Source dataset
uspto-grants-1998_03
Patent number
US05731364

Linked notes

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