Phosphorus tribromide → 5-(2-bromoethyl)-2,3-dihydro-1H-indene

HRID 1608797Notes

Reaction equation

HRID 1608797 reaction equation
P(Br)(Br)[Br:2].O[CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[CH2:13][CH2:12][CH2:11]2>C(Cl)(Cl)(Cl)Cl>[Br:2][CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[CH2:13][CH2:12][CH2:11]2

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 212240872-(2,3-dihydro-1H-inden-5-yl)ethan-1-ol

Product 1

HCID 212240805-(2-bromoethyl)-2,3-dihydro-1H-indene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

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 solution. The layers were separated and the aqueous layer extracted twice with dichloromethane. The combined dichloromethane extracts were dried (MgSO4) and evaporated to give an oil which was purified by column chromatography on silica using dichloromethane as the eluant. Appropriate fractions were combined and concentrated in vacuo to give the title compound as a colourless oil, yield 10.5 g.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. customthe mixture partitioned between dichloromethane and 10% aqueous sodium carbonate solution
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted twice with dichloromethane
  6. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  7. customevaporated
  8. customto give an oil which
  9. customwas purified by column chromatography on silica
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ed45ba059c2e49609c9f387782e9082b
Source dataset
uspto-grants-1995_03
Patent number
US05397800

Reaction notes

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