Hydrochloric Acid → 1-Chloro-3-(chloromethyl)-2-[(phenylmethyl)thio]benzene

Participants

Reaction Conditions

Reaction Steps

To a mixture of 54 g of the compound of Example 2 in 200 mL of chloroform (ethanol-free) and of N,N-dimethylaniline, a solution of 30 g of thionyl chloride in 50 mL of chloroform (ethanol-free) was added while maintaining the reaction temperature at 15° C. with an ice-water bath. The mixture was stirred at 25° C. for 1 hour, then refluxed for 3 hours. The mixture was acidified with 1 N aqueous hydrochloric acid and the organic layer was collected. The organic layer was washed once with 1 N aqueous hydrochloric acid, dried over magnesium sulfate, and filtered. The filtrate was passed through a silica gel column, eluted with methylene chloride, and after evaporation of the eluant, 54 g subject compound was obtained as a yellow oil.

Provenance & Evidence