反応 #4176

反応方程式

dichloromethane

5-Bromoindoline

collidine

o-fluoronitrobenzene

→

product

収率 55.0%

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

収率 55.0%

溶媒

xylene

反応条件

後処理

1. 1
   洗浄The dichloromethane solution was washed with 1N hydrochloric acid (3 times, 150 ml), brine (200 ml)
2. 2
   乾燥dried over anhydrous magnesium sulfate
3. 3
   ろ過filtered
4. 4
   その他The solvent was evaporated
5. 5
   その他Crystallization of the residue
6. 6
   温度chilling in the refrigerator overnight
7. 7
   ろ過The solid was filtered
8. 8
   洗浄washed with hexane
9. 9
   その他dried

実験手順

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.

出典