Reaction #1726669

Reaction equation

hydrogen bromide

di(4-chlorophenyl)sulfoxide

trimethylchlorosilane

4-bromochlorobenzene

→

tris(4-chlorophenyl)sulfonium Bromide

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Otherkept at 0 to 5° C.
2. 2
   workup.ADDITIONwas added dropwise over the period of 30 min into the reaction vessel
3. 3
   workup.STIRRINGAfter agitated for one hr at 0° C.
4. 4
   workup.WAITfollowed by another hr
5. 5
   workup.ADDITIONagitation at room temperature, the reaction solution was slowly poured into an aqueous solution
6. 6
   Extractionextracted with 250 ml dichloromethane
7. 7
   DryingThe extract was dried with sodium sulfate

Procedure

Under a nitrogen atmosphere, 16.3 g (0.06 mol) of di(4-chlorophenyl)sulfoxide was dissolved in 250 ml dichloremethane. Into the resulting solution kept at 0 to 5° C., 10.8 g (0.10 mol) of trimethylchlorosilane was added dropwise; the mixture was stirred at 0° C. for 30 min. Thereafter, 200 g of a tetrahydrofuran (THF) solution of the Grignard reagent prepared by the usual process with 4-bromochlorobenzene (0.18 mol) was added dropwise over the period of 30 min into the reaction vessel cooled with 0 to 10° C. ice water. After agitated for one hr at 0° C., followed by another hr agitation at room temperature, the reaction solution was slowly poured into an aqueous solution containing 250 ml of an aqueous 12% hydrogen bromide solution and ice, then extracted with 250 ml dichloromethane. The extract was dried with sodium sulfate.

Source