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

HRID 990110Notes

Reaction equation

HRID 990110 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]O)=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:20]>C(OCC)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][Br:20])=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 988324-Benzyloxy-3-methoxybenzyl alcohol

Product 1

HCID 3258374-(Benzyloxy)-3-methoxybenzyl bromideYield 192.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 4-(benzyloxy)-3-methoxybenzyl alcohol (9.0 g, 36.84 mmol) in anhydrous diethyl ether (150 mL) was slowly added PBr3 (4.99 g, 18.42 mmol) via syringe, and the resulting mixture was stirred at room temperature for 3 hours. The mixture was diluted with diethyl ether (100 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 4-(benzyloxy)-3-methoxybenzyl bromide (10.9 g, 96%) 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-0942bb781a0745848da9206a7d2ccb8f
Source dataset
uspto-grants-2002_10
Patent number
US06458829B1

Reaction notes

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