Hydrogen Bromide → Triphenylsulfonium Bromide

Participants

Reaction Steps

In 600 ml of tetrahydrofuran were dissolved, 21.1 g (0.1 mol) of diphenylsulfoxide under nitrogen atmosphere, then 27.2 g (0.25 mol) of chlorotrimetylsilane was poured into them. A Grignard reagent prepared from 39.3 g (0.25 mol) of bromobenzene and 6.1 g of magnesium metal in accordance with the conventional manner was added dropwise thereto under ice-cooling, followed by allowing to react at the same temperature for 3 hours. After completion of the reaction, 500 ml of 24% aqueous solution of hydrobromic acid was added dropwise to the reaction solution at 0 to 5° C., and then 600 ml of toluene was poured into them, followed by stirring and separation, the organic layer was extracted twice with 120 ml of 12% aqueous solution of hydrobromic acid, and the resulting aqueous layers were combined and extracted 3 times with 480 ml of methylene chloride. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 23.3 g (yield: 68%) of triphenylsulfonium bromide as a white crystal.

Provenance & Evidence