Reaction #1903

Reaction equation

4-bromo-3-methoxyphenol

benzyl bromide

potassium carbonate

→

4-benzyloxy-2-methoxybromobenzene

Solvents

acetone

Conditions

Workup

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

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.

Source