반응 #160837

반응 방정식

Trichloracetyl chloride

aluminum trichloride

2-cyanopyrrole

→

desired product

수율 100.8%

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

수율 100.8%

용매

ethyl acetate

dichloromethane

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   온도The reaction was heated
2. 2
   온도at reflux for 5 h
3. 3
   온도to cool
4. 4
   기타quenched slowly with water (300 mL)
5. 5
   기타The layers were separated
6. 6
   세척the organic layer was washed with water and brine
7. 7
   건조dried (magensium sulfate)
8. 8
   기타evaporated under reduced pressure

실험 절차

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).

출처