반응 #214482

반응 방정식

water

ethyl 6-bromo-5-chloro-3-phenylindole-2-carboxylate

dimethylsulfoxide

sodium hydride

dimethylsulfoxide

acetic acid

water

→

6-bromo-5-chloro-2[(methylsulfinyl)acetyl]-3-phenylindole

용매

benzene

benzene

반응 조건

후처리

1. 1
   온도heat at 65°-75° for 2 hours under nitrogen
2. 2
   온도Cool the resulting mixture to 15° C.
3. 3
   workup.STIRRINGstir
4. 4
   여과filter
5. 5
   세척Wash the resulting solid with water
6. 6
   기타Crystallize the desired product from methanol-methylene chloride

실험 절차

Stir sodium hydride (13 g) in a mixture of dimethylsulfoxide (100 ml) and benzene (100 ml), and heat at 65°-75° for 2 hours under nitrogen. To this mixture add ethyl 6-bromo-5-chloro-3-phenylindole-2-carboxylate in dimethylsulfoxide (50 ml) and benzene (30 ml) at 15°-20° and stir the mixture at room temperature for one hour. Cool the resulting mixture to 15° C. add 50 ml of water (very slowly) and then add an additional 550 ml of water. Add 25 ml of acetic acid, stir and then filter. Wash the resulting solid with water and then hexane. Crystallize the desired product from methanol-methylene chloride to obtain 6-bromo-5-chloro-2[(methylsulfinyl)acetyl]-3-phenylindole, m.p. 169°-170°.

출처