Hydrochloric Acid → 2,3,6-Trichloro-4-(trifluoromethyl)aniline

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Reaction Steps

A mixture of 3-chloro-4-trifluoromethylaniline [20 g; described in British Patent Specification No. 459890] and hydrochloric acid (d: 1.18; 12 ml) was suspended in water (600 ml). Chlorine gas (from 13 ml of liquid chlorine) was then passed into the stirred suspension with heating at reflux. On completion of the addition of chlorine gas, stirring was continued for a further 15 minutes. After cooling, the solution thus obtained was extracted with dichloromethane (3×250 ml). The combined organic extracts were washed with water, saturated aqueous solid bicarbonate solution and water, dried over anhydrous sodium sulphate and evaporated. The red oil thus obtained was distilled (bp 143°-147° C./20 mmHg) to give an orange oil which crystallized on standing to give 2,3,6-trichloro-4-trifluoromethylaniline (12.26 g), m.p. 37°-39° C., in the form of an orange solid.

Provenance & Evidence