反应详情

温度

57.5 °C

2-Chloro-6-iodo-4-(trifluoromethyl)benzenamine (i.e. the product of Example 4) (31.8 g, 98.9 mmol) was added to hydrochloric acid (36%, 190 mL) and the mixture was warmed to 55-60° C. for 20 min. The mixture was cooled to 0° C. Sodium nitrite (13.6 g, 197 mmol) in water (36 mL) was added over 30 min. When the addition was complete the mixture was stirred at 0-5° C. for 70 min. Hypophosphorous acid (50%, 36.5 mL, 351 mmol) was added dropwise at 5-10° C. over 40 min. When the addition was complete the mixture spontaneously warmed briefly to 35° C., and was then cooled to 10-20° C. After stirring at 10-20° C. for 2 h, the mixture was stored in a refrigerator overnight. Then the mixture was warmed to room temperature and was stirred for 1 h. The mixture was diluted with water (400 mL) and extracted with ether (2×250 mL). The combined extracts were dried and evaporated. Distillation gave the product as an oil (19.93 g, 66% yield), b.p. 98-112° C. at 2.0 kPa.

1. temperatureThe mixture was cooled to 0° C
2. additionWhen the addition
3. additionWhen the addition
4. temperaturespontaneously warmed briefly to 35° C.
5. temperaturewas then cooled to 10-20° C
6. stirringAfter stirring at 10-20° C. for 2 h
7. customwas stored in a refrigerator overnight
8. temperatureThen the mixture was warmed to room temperature
9. stirringwas stirred for 1 h
10. extractionextracted with ether (2×250 mL)
11. customThe combined extracts were dried
12. customevaporated
13. distillationDistillation