1-Bromo-2-Chloroethane → 1-Chloro-4-[(2-chloroethyl)thio]benzene

Participants

Reaction Conditions

Reaction Steps

A mixture consisting of 12.21 g (56.5 mmoles) of 4-chlorophenylthio(trimethyl)silane, 20 ml of hexamethylphosphoric triamide and 18.7 ml (226 mmoles) of 1-bromo-2-chloroethane was heated at 60° C. and it was established that the conversion was complete after 10 minutes. After treating the reaction mixture as described in Example 3, there were obtained 10.03 g (85.7% yield) of 2-chloroethyl 4-chlorophenyl sulfide boiling at 105°-109° C./1.0 mm Hg and melting at 28°-29° C. The residue of the distillation contained 1,2-bis(4-chlorophenylthio)ethane as a by-product which after crystallization from methanol melted at 87°-88° C.

Provenance & Evidence