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

HRID 1835299Notes

Reaction equation

HRID 1835299 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-6d9d7ef04d644204b0d156a96370fbef
Source dataset
uspto-grants-2004_08
Patent number
US06770658B2

Reaction notes

Loading…