Phosphorus tribromide → 1-Bromo-2-(2-bromoethyl)benzene

HRID 1076568Notes

Reaction equation

HRID 1076568 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5]O.P(Br)(Br)[Br:12]>>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][Br:12]

Participants

3

Reactant 2

HCID 24614Phosphorus tribromideHCID 27340892-(2-Bromophenyl)ethan-1-ol

Product 1

HCID 3340691-Bromo-2-(2-bromoethyl)benzeneYield 145.2%

Procedure

To 550.0 g of o-bromophenethyl alcohol, while stirring, is added, dropwise, 375.0 g of phosphorus tribromide. After stirring for three hours at room temperature, the reaction mixture is heated on a steam bath for three hours and then poured into 6 kg of crushed ice. The mixture is extracted with three 600 and two 200 ml portions of ether. The ether extracts are washed, dried, concentrated, and the residue is distilled to give 531.0 g of o-bromophenethyl bromide, bp. about 86°-88° (0.9mm), nD26 1.5922.

Workup

  1. additionis added
  2. temperaturethe reaction mixture is heated on a steam bath for three hours
  3. extractionThe mixture is extracted with three 600 and two 200 ml portions of ether
  4. washThe ether extracts are washed
  5. customdried
  6. concentrationconcentrated
  7. distillationthe residue is distilled

Sources & evidence

ORD record
ord-6c8ee9ba8a5c4beda712b5b9442e68a1
Source dataset
uspto-grants-1976_05
Patent number
US03957787

Reaction notes

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