Reacción #63404

Ecuación de reacción

dichloromethane

5-Bromoindoline

collidine

o-fluoronitrobenzene

→

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

Disolventes

xylene

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe dichloromethane solution was washed with 1N hydrochloric acid (3 times, 150 ml), brine (200 ml)
2. 2
   Secadodried over anhydrous magnesium sulfate
3. 3
   Filtraciónfiltered
4. 4
   OtroThe solvent was evaporated
5. 5
   OtroCrystallization of the residue
6. 6
   Temperaturachilling in the refrigerator overnight
7. 7
   FiltraciónThe solid was filtered
8. 8
   Lavadowashed with hexane
9. 9
   Otrodried
10. 10
    Otroto yield 3.5 g (55%
11. 11
    OtroRecrystallization from 2-propanol
12. 12
    Otroyielded the analytical sample, mp 112°-114° C.

Procedimiento

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 112°-114° C.

Fuente