Phosphorus tribromide → 1-(3-Bromopropyl)-4-methoxybenzene

HRID 2301926Notes

Reaction equation

HRID 2301926 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11]O)=[CH:5][CH:4]=1.P(Br)(Br)[Br:14]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][Br:14])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 794063-(4-Methoxyphenyl)-1-propanol

Product 1

HCID 127769961-(3-Bromopropyl)-4-methoxybenzeneYield 61.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-(p-methoxyphenyl)-1-propanol (16.6 g; 0.1 mol) in 250 mL of toluene, cooled to 0° C., was added dropwise 26 mL of phosphorus tribromide (0.27 mol). Following completion of the addition, the reaction was stirred at room temperature for 1 hour, then refluxed for an additional hour. The reaction was cooled and poured onto ice, the layers were separated, and the organic phase washed with saturated sodium bicarbonate (3×) and brine (3×). The crude material obtained upon drying and evaporation of the solvent was chromatographed, eluting with 10% EtOAc/hexane, to obtain 14 g (61%) of 3-(p-methoxyphenyl)-1-propylbromide.

Workup

  1. additioncompletion of the addition
  2. temperaturerefluxed for an additional hour
  3. temperatureThe reaction was cooled
  4. additionpoured onto ice
  5. customthe layers were separated
  6. washthe organic phase washed with saturated sodium bicarbonate (3×) and brine (3×)
  7. customThe crude material obtained
  8. customupon drying
  9. customevaporation of the solvent
  10. customwas chromatographed
  11. washeluting with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-39303c96917a490c95f73896e9e201ab
Source dataset
uspto-grants-2002_08
Patent number
US06429215B1

Reaction notes

Loading…