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

HRID 1835292Notes

Reaction equation

HRID 1835292 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-c2799c0b6a1d4a6cbe342d98de75af34
Source dataset
uspto-grants-2004_08
Patent number
US06770658B2

Reaction notes

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