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

HRID 36858Notes

Reaction equation

HRID 36858 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 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.

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 wilth dichloromethane (2×100 ml)
  6. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give an oil which
  9. customwas purified by column chromatography on silica eluting with dichloromethane
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d801bc8a3c7c40d68f51399fe0121c81
Source dataset
uspto-grants-1995_05
Patent number
US05418229

Reaction notes

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