Reacción #65136

Ecuación de reacción

Phosphorus tribromide

5-(2-hydroxyethyl)indane

→

title compound

5-(2-Bromoethyl)indane

Disolventes

carbon tetrachloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturaunder reflux for 2 hours
3. 3
   Otrothe mixture partitioned between dichloromethane and 10% aqueous sodium carbonate solution
4. 4
   OtroThe layers were separated
5. 5
   Extracciónthe aqueous layer extracted wilth dichloromethane (2×100 ml)
6. 6
   SecadoThe combined dichloromethane extracts were dried (MgSO4)
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   Otroto give an oil which
9. 9
   Otrowas purified by column chromatography on silica eluting with dichloromethane
10. 10
    Concentraciónconcentrated in vacuo

Procedimiento

Phosphorus tribromide (3.5 ml) was added, dropwise, to a solution of 5-(2-hydroxyethyl)indane (14.0 g) (FR-A-2139628) in carbon tetrachloride (100 ml). The mixture was stirred at room temperature for 0.5 hour and then heated under reflux for 2 hours. Ice (100 g) was added and the mixture partitioned between dichloromethane and 10% aqueous sodium carbonate solution. The layers were separated and the aqueous layer extracted wilth dichloromethane (2×100 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give an oil which was purified by column chromatography on silica eluting with dichloromethane. The product-containing fractions were combined and concentrated in vacuo to give the title compound as a colourless oil, yield 10.5 g.

Fuente