Phosphorus tribromide → (5-Bromopentyl)benzene

HRID 484337

Reaction equation

HRID 484337 reaction equation
P(Br)(Br)[Br:2].[C:5]1([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]O)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(Cl)(Cl)Cl>[C:5]1([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][Br:2])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromide2×HCID 615235-Phenyl-1-pentanol

Product 1

HCID 285561(5-Bromopentyl)benzene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 1.8 g (6.7 mmol) amount of phosphorus tribromide was added to a chloroform solution (20 ml) of 3.3 g (20 mmol) of 5-phenyl-1-pentanol and the resulting solution was heated at reflux for 4 hours. When the reaction was traced by TLC, the starting materials were found to still remain in the reaction mixture, and so 0.2 g of phosphorus tribromide was further added and heated at reflux. Afterwards, the reaction solution was washed with water and dried with anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. Thus, 4.30 g of a crude 5-phenylpentyl bromide was obtained.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux for 4 hours
  3. additionwas further added
  4. temperatureheated
  5. temperatureat reflux
  6. washAfterwards, the reaction solution was washed with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-37c2e7860e4e4a2284712f3d40aed8d0
Source dataset
uspto-grants-1993_07
Patent number
US05231105

Linked notes

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