Phosphorus tribromide → 1-(2-Bromoethyl)-4-chlorobenzene

HRID 1587868Notes

Reaction equation

HRID 1587868 reaction equation
P(Br)(Br)[Br:2].[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([CH2:10][CH2:11]O)=[CH:8][CH:7]=1>C(Cl)(Cl)(Cl)Cl>[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([CH2:10][CH2:11][Br:2])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 74647p-Chlorophenethylic alcohol

Product 1

HCID 230291-(2-Bromoethyl)-4-chlorobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Phosphorus tribromide (1.3 ml) was added, dropwise, to a solution of 4-chlorophenethyl alcohol (5.0 g) in carbon tetrachloride (30 ml). The mixture was stirred at room temperature for 10 minutes then heated under reflux for 2 hours. Ice (50 g) was added and the mixture partitioned between dichloromethane (50 ml) and 10% aqueous sodium carbonate (50 ml). The layers were separated and the aqueous layer extracted with dichloromethane (2×50 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 3.0 g.

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 2 hours
  3. customthe mixture partitioned between dichloromethane (50 ml) and 10% aqueous sodium carbonate (50 ml)
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted with dichloromethane (2×50 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-f4cc1d6066e7413587bebdc4989d0afa
Source dataset
uspto-grants-1993_06
Patent number
US05219871

Reaction notes

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