Dichloromethane → Triphenylsulfonium 4-trifluoromethylbenzenesulfonate

HRID 2914

Reaction equation

HRID 2914 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-:16].[Na+].[Na+].[Cl-].[C:22]1([S+:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[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.ClCCl>O>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O-:16])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[C:35]1([S+:28]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 61343Triphenylsulfonium chlorideHCID 27773994-(Trifluoromethyl)benzenesulfonyl chloride

Product 1

HCID 22057398Triphenylsulfonium 4-trifluoromethylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 4-trifluoromethylbenzenesulfonyl chloride (20.53 g, 83.9 mmol) in water (150 ml) containing sodium carbonate (9.43 g, 88.10 mmol) was heated at reflux for 22 hours. After cooling to room temperature, triphenylsulfonium chloride (50% aqueous solution, 50.00 g) was added over 15 minutes. After stirring the biphasic mixture for 30 minutes, dichloromethane (300 ml) was added and the mixture stirred at room temperature for 20 hours. The layers were separated and the organic layer washed with water (7×150 ml) until the washings were neutral (pH 7 ). After drying (MgSO4 ), removal of the solvent in vacuo gave a pale yellow foam which was further dried by heating at 80°-100° C. for 108 hours under vacuum. In this way, triphenylsulfonium 4 -trifluoromethylbenzenesulfonate was isolated as a pale yellow glass (36.77 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 22 hours
  3. stirringthe mixture stirred at room temperature for 20 hours
  4. customThe layers were separated
  5. washthe organic layer washed with water (7×150 ml) until the washings
  6. customAfter drying
  7. custom(MgSO4 ), removal of the solvent in vacuo
  8. customgave a pale yellow foam which
  9. customwas further dried
  10. temperatureby heating at 80°-100° C. for 108 hours under vacuum

Sources & evidence

ORD record
ord-36355329f50b4fba91d75f1d3bd8c47f
Source dataset
uspto-grants-1998_03
Patent number
US05731364

Linked notes

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