반응 #4176

반응 방정식

dichloromethane

5-Bromoindoline

collidine

o-fluoronitrobenzene

→

product

수율 55.0%

5-Bromo-1-(2-nitrophenyl)indoline

수율 55.0%

용매

xylene

반응 조건

후처리

1. 1
   세척The dichloromethane solution was washed with 1N hydrochloric acid (3 times, 150 ml), brine (200 ml)
2. 2
   건조dried over anhydrous magnesium sulfate
3. 3
   여과filtered
4. 4
   기타The solvent was evaporated
5. 5
   기타Crystallization of the residue
6. 6
   온도chilling in the refrigerator overnight
7. 7
   여과The solid was filtered
8. 8
   세척washed with hexane
9. 9
   기타dried

실험 절차

5-Bromoindoline (4.0 g, 0.02 mole), collidine (3.6 g, 0.03 mole), and o-fluoronitrobenzene (2.8 g, 0.02 mole) in xylene (25 ml) were heated at 185° C. (oil bath temperature) for 24 hours. The mixture was cooled to room temperature and poured into dichloromethane. The dichloromethane solution was washed with 1N hydrochloric acid (3 times, 150 ml), brine (200 ml), dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated. Crystallization of the residue was induced by stirring in ether (15 ml) followed by hexane (200 ml), then chilling in the refrigerator overnight. The solid was filtered and washed with hexane and dried to yield 3.5 g (55%) of product. Recrystallization from 2-propanol yielded the analytical sample, mp 12°-114° C.

출처