Reaktion #4176

Reaktionsgleichung

dichloromethane

5-Bromoindoline

collidine

o-fluoronitrobenzene

→

product

Ausbeute 55.0%

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

Ausbeute 55.0%

Lösungsmittel

xylene

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe dichloromethane solution was washed with 1N hydrochloric acid (3 times, 150 ml), brine (200 ml)
2. 2
   Trocknendried over anhydrous magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   SonstigeThe solvent was evaporated
5. 5
   SonstigeCrystallization of the residue
6. 6
   Temperaturchilling in the refrigerator overnight
7. 7
   FiltrationThe solid was filtered
8. 8
   Waschenwashed with hexane
9. 9
   Sonstigedried

Vorschrift

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.

Quelle