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

HRID 1463876Notes

Reaction equation

HRID 1463876 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-83f115f3b0ce4f1296e02f939f265ce7
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

Loading…