Hydrogen Bromide → (4-Methylphenyl)(diphenyl)sulfanium bromide

Participants

Reaction Steps

In a 4-methylphenyl Grignard reagent of 1.32 L (1.88 mol, 1.42 mol/L, 2.5 equiv.) prepared by a common method from 4-bromotoluene and magnesium as raw materials using tetrahydrofuran (THF) as a solvent was added a solution dissolving diphenyl sulfoxide of 151.71 g (0.75 mol, 1 equiv.) and chlorotrimethylsilane (TMSCl) of 407.25 g (3.75 mol, 5 equiv.) in THF of 0.6 L at −5° C. to room temperature, followed by reacting under stirring for 30 minutes. After termination of the reaction, the resultant reaction mixture was poured into 12% hydrobromic acid of 1.1 L and extracted two times with dichloromethane of 1.8 L. The obtained product was washed with water and then concentrated to dryness and crystallized in acetone of 1.8 L to obtain the product of 203.7 g as a white crystal (yield: 76%). Property data thereof are shown in Table 1.

Provenance & Evidence