Reaction #4118

Reaction equation

dichloromethane

5-Bromoindoline

collidine

o-fluoronitrobenzene

→

product

Yield 55.0%

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

Yield 55.0%

Solvents

xylene

Conditions

Workup

1. 1
   WashThe dichloromethane solution was washed with 1N hydrochloric acid (3 times, 150 ml), brine (200 ml)
2. 2
   Dryingdried over anhydrous magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   OtherThe solvent was evaporated
5. 5
   OtherCrystallization of the residue
6. 6
   Temperaturechilling in the refrigerator overnight
7. 7
   FiltrationThe solid was filtered
8. 8
   Washwashed with hexane
9. 9
   Otherdried

Procedure

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.

Source