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

HRID 1414212Notes

Reaction equation

HRID 1414212 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 3 hours at room temperature, the reaction mixture is heated on a steam bath for 3 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 3 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-998766895c444fcfa9f8ecbf888bd0a6
Source dataset
uspto-grants-1977_01
Patent number
US04001233

Reaction notes

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