Chlorotrimethylsilane → (4-tert-Butoxyphenyl)(diphenyl)sulfanium chloride

Participants

Reaction Steps

A solution of 20.2 g (0.10 mol) of diphenyl sulfoxide in 200 g of methylene chloride was cooled on an ice bath. To the solution, 5.3 g (0.052 mol) of triethylamine was added and 32.6 g (0.30 mol) of trimethylsilyl chloride was dropwised at 0° to 20° C. Stirring was continued at 0° to 10° C. for 15 minutes. To this solution, a Grignard reagent which was conventionally prepared from 55.4 g (0.30 mol) of 4-tert-butoxychlorobenzene, 7.3 g (0.30 mol) of magnesium, and 90 g of THF was dropwised at 0° to 10° C. Stirring was continued at 0° to 10° C. for 30 minutes. 500 g of 20% ammonium chloride aqueous solution was added to the reaction mixture. To the organic layer was added 1,000 g of chloroform. The organic layer was once washed with 200 g of water and evaporated. The residue was purified by recrystalization, isolating 26.6 g (yield 72%) of (4-tert-butoxyphenyl)diphenylsulfonium chloride with 98% purity.

Provenance & Evidence