4-Chloroaniline → HCID 86745778, compound

Participants

Reaction Steps

To a DMF (50 mL) solution of 4-chloroaniline (3.0 g, 23.5 mmol) was added ethenesulfonyl fluoride (3.3 mL, 30 mmol). The solution was heated at 110° C. until the 4-chloroaniline was consumed (monitored by tlc). The orange solution was diluted with 1 liter of water and the resulting oily precipitate was extracted into ether. The combined organic layers was washed with water and brine and dried (MgSO4). After the ether had been removed by distillation, the brown residue afforded the title compound (4.56 g, 81%) as yellow needles which could be crystallized from ether/hexane, mp 61°-63° C. (lit. mp 62°-63° C.; Hoechst's German Patent 1104968).

Provenance & Evidence