반응 #40901

반응 방정식

ammonium chloride

7-bromoindole

4-chlorobutyronitrile

ethylmagnesium bromide

→

titled compound

4-(7-bromo-1H-indol-3-yl)butanenitrile

용매

toluene

반응 조건

후처리

1. 1
   온도the mixture was heated
2. 2
   온도to reflux for 4.5 hours
3. 3
   추출followed by extraction with ethyl acetate
4. 4
   세척The organic layer was washed in turn with water and saturated saline
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   농축concentrated
7. 7
   기타The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10→70:30)

실험 절차

To an anhydrous toluene (12 mL) solution of 7-bromoindole (1.0 g) and 4-chlorobutyronitrile (0.26 g), ethylmagnesium bromide (3.0M diethyl ether solution; 1.7 mL) was added dropwise under ice cooling and the mixture was heated to reflux for 4.5 hours. To the reaction mixture, an aqueous saturated ammonium chloride solution was added under ice cooling, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and saturated saline, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10→70:30) to obtain the titled compound having the following physical properties (0.40 g).

출처