Phosphorus tribromide → 3-(Propyloxy)-4-methoxybenzyl bromide

HRID 990117Notes

Reaction equation

HRID 990117 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH2:8]O)[CH2:2][CH3:3].P(Br)(Br)[Br:16]>C(OCC)C>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH2:8][Br:16])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 28562459(4-Methoxy-3-propoxyphenyl)methanol

Product 1

HCID 235035423-(Propyloxy)-4-methoxybenzyl bromideYield 193.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 3-(propyloxy)-4-methoxybenzyl alcohol (2.28 g, 11.62 mmol) in anhydrous diethyl ether (30 mL) was slowly added PBr3 (0.55 mL, 5.81 mmol) via syringe, and the resulting mixture was stirred at room temperature for 2 hours. The mixture was diluted with diethyl ether (150 mL) and washed with saturated aqueous NaHCO3 (2×75 mL) and brine (2×75 mL). The organic layer was dried over anhydrous MgSO4, and the solvent was removed under reduced pressure to afford 3-(propyloxy)-4-methoxybenzyl bromide (2.92 g, 97%) as a white solid.

Workup

  1. washwashed with saturated aqueous NaHCO3 (2×75 mL) and brine (2×75 mL)
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-30ef0e80001a46449e9cbfb3f4adc65b
Source dataset
uspto-grants-2002_10
Patent number
US06458829B1

Reaction notes

Loading…