Benzyl Bromide → 4-(Benzyloxy)-1-bromo-2-methoxybenzene

HRID 1419062Notes

Reaction equation

HRID 1419062 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:9][CH3:10].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:11]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([O:9][CH3:10])[CH:4]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 3479554-Bromo-3-methoxyphenol

Product 1

HCID 129859234-(Benzyloxy)-1-bromo-2-methoxybenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-bromo-3-methoxyphenol (21 g), benzyl bromide (13.5 ml), potassium carbonate (21.4 g) and acetone (200 ml) was stirred at room temperature for 24 h. The insoluble materials were removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate 20:1) to give 4-benzyloxy-2-methoxybromobenzene (25 g) as an oil.

Workup

  1. customThe insoluble materials were removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate 20:1)

Sources & evidence

ORD record
ord-4fdea8f203cf42dfb44e768991de59f7
Source dataset
uspto-grants-1999_03
Patent number
US05885979

Reaction notes

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