Reaction #3010

Reaction equation

triphenylsulfonium chloride

dichloromethane

4-trifluoromethylbenzenesulfonyl chloride

sodium carbonate

→

triphenylsulfonium 4 -trifluoromethylbenzenesulfonate

Solvents

water

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureat reflux for 22 hours
3. 3
   workup.STIRRINGthe mixture stirred at room temperature for 20 hours
4. 4
   OtherThe layers were separated
5. 5
   Washthe organic layer washed with water (7×150 ml) until the washings
6. 6
   OtherAfter drying
7. 7
   Other(MgSO4 ), removal of the solvent in vacuo
8. 8
   Othergave a pale yellow foam which
9. 9
   Otherwas further dried
10. 10
    Temperatureby heating at 80°-100° C. for 108 hours under vacuum

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).

Source