Reaction #640565

Reaction equation

hydrochloric acid

magnesium

chlorobenzene

trimethylsilyl chloride

Diphenyl sulfoxide

→

triphenylsulfonium chloride

Solvents

diethyl ether

water

tetrahydrofuran

water

dichloromethane

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise at a temperature below 20° C
2. 2
   workup.WAITThe reaction solution was aged for one hour
3. 3
   Otherto quench
4. 4
   Otherthe reaction
5. 5
   OtherThe water layer was separated
6. 6
   Washwashed with 100 g of diethyl ether

Procedure

Diphenyl sulfoxide, 40 g (0.2 mole), was dissolved in 400 g of dichloromethane, which was stirred under ice cooling. At a temperature below 20° C., 65 g (0.6 mole) of trimethylsilyl chloride was added dropwise to the solution, which was aged for 30 minutes at the temperature. Then, a Grignard reagent which had been prepared from 14.6 g (0.6 mole) of metallic magnesium, 67.5 g (0.6 mole) of chlorobenzene and 168 g of tetrahydrofuran (THF) was added dropwise at a temperature below 20° C. The reaction solution was aged for one hour, after which 50 g of water at a temperature below 20° C. was added to quench the reaction. To this solution, 150 g of water, 10 g of 12N hydrochloric acid, and 200 g of diethyl ether were further added. The water layer was separated and washed with 100 g of diethyl ether, yielding an aqueous solution of triphenylsulfonium chloride. The compound in aqueous solution form was used in the subsequent reaction without further isolation.

Source