Reaction #49680

Reaction equation

Phosphorus tribromide

5-(2-hydroxyethyl)indane

→

title compound

5-(2-bromoethyl)indane

Solvents

carbon tetrachloride

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureunder reflux for 2 hours
3. 3
   Otherthe mixture partitioned between dichloromethane and 10% aqueous sodium carbonate
4. 4
   OtherThe layers were separated
5. 5
   Extractionthe aqueous layer extracted with dichloromethane (2×100 ml)
6. 6
   DryingThe combined dichloromethane extracts were dried (MgSO4)
7. 7
   Concentrationconcentrated in vacuo
8. 8
   Otherto give an oil which
9. 9
   Otherwas purified by column chromatography on silica eluting with dichloromethane
10. 10
    Concentrationconcentrated in vacuo

Procedure

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. The layers were separated and the aqueous layer extracted with 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.

Source