Benzenemethanol, 2-(phenylmethoxy)- → 2-Benzyloxybenzylbromide

HRID 2395046Notes

Reaction equation

HRID 2395046 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:18]>C(OCC)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][Br:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 18811Benzenemethanol, 2-(phenylmethoxy)-HCID 24614Phosphorus tribromide

Product 1

HCID 15142522-BenzyloxybenzylbromideYield 94.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a solution of 2-benzyloxybenzyl alcohol (4.83 g) in diethyl ether (40 ml) was added dropwise, at 0° C., a solution of phosphorus tribromide (6.27 g) in diethyl ether (10 ml). The mixture was warmed to ambient temperature, diluted with diethyl ether (100 ml) and filtered through a pad of silica gel washing with 1 litre of diethyl ether. The combined organic solution was washed with saturated aqueous sodium hydrogen carbonate (100 ml) and brine (100 ml), dried (sodium sulphate), filtered and evaporated to give 2-benzyloxybenzyl bromide (5.88 g) as an oil.

Workup

  1. filtrationfiltered through a pad of silica gel washing with 1 litre of diethyl ether
  2. washThe combined organic solution was washed with saturated aqueous sodium hydrogen carbonate (100 ml) and brine (100 ml)
  3. dry with materialdried (sodium sulphate)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-b87a5c633f51404e921203fca8017be6
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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