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

HRID 484330Notes

Reaction equation

HRID 484330 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-indeneYield 54%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Phosphorous tribromide (3.5 ml) was added, dropwise, to an ice-cooled solution of 5-(2-hydroxyethyl)indane (prepared as described in FR-2,139,628) (14.0 g) in carbon tetrachloride (100 ml) and the mixture was heated under reflux for 2 hours, quenched with ice-water and partitioned between dichloromethane and 10% aqueous sodium carbonate solution. The organic layer was washed with water, dried over magnesium sulphate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel using dichloromethane as eluant. Appropriate fractions were combined and evaporated under reduced pressure to give the title compound as a pale yellow oil, (10.5 g, 54%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customquenched with ice-water
  4. custompartitioned between dichloromethane and 10% aqueous sodium carbonate solution
  5. washThe organic layer was washed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by chromatography on silica gel
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8aac7c49e9074aa6a9df8c838d80595f
Source dataset
uspto-grants-1993_07
Patent number
US05231104

Reaction notes

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