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

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.

1. temperaturewith heating
2. temperatureat reflux
3. temperatureAfter cooling
4. customthe solution thus obtained
5. extractionwas extracted with dichloromethane (3×250 ml)
6. washThe combined organic extracts were washed with water, saturated aqueous solid bicarbonate solution and water
7. dry with materialdried over anhydrous sodium sulphate
8. customevaporated
9. customThe red oil thus obtained
10. distillationwas distilled (bp 143°-147° C./20 mmHg)
11. customto give an orange oil which
12. customcrystallized

ORD record

ord-abbc767e10c945c7b3e9b2555f71b22e

Source dataset

uspto-grants-1985_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04541963