Реакция #160837

Уравнение реакции

Trichloracetyl chloride

aluminum trichloride

2-cyanopyrrole

→

desired product

Выход 100.8%

4-(trichloroacetyl)-1H-pyrrole-2-carbonitrile

Выход 100.8%

Растворители

ethyl acetate

dichloromethane

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   ТемператураThe reaction was heated
2. 2
   Температураat reflux for 5 h
3. 3
   Температураto cool
4. 4
   Другоеquenched slowly with water (300 mL)
5. 5
   ДругоеThe layers were separated
6. 6
   Промывкаthe organic layer was washed with water and brine
7. 7
   Сушкаdried (magensium sulfate)
8. 8
   Другоеevaporated under reduced pressure

Методика

Trichloracetyl chloride (44.4 g, 27.3 mL, 244 mmol) in dichloromethane (75 mL) was added over 20 min to a mechanically stirred suspension of aluminum trichloride (54.3 g, 407 mmol) in dichloromethane (150 mL). The resulting mixture was stirred for 30 min, and then 2-cyanopyrrole (15.0 g, 163 mmol) in dichloromethane (75 mL) was added over 30 min. The reaction was heated at reflux for 5 h and then allowed to cool. The reaction was diluted with ethyl acetate (600 mL) and then quenched slowly with water (300 mL). The layers were separated and then the organic layer was washed with water and brine, dried (magensium sulfate) and evaporated under reduced pressure to afford a quantitative yield of desired product (39.0 g, 100%) containing trace impurities. This material was used in the next step without further purification. 1H NMR (DMSO-d6) δ 8.14 (s, 1H), 7.55 (s, 1H).

Источник