Reaction #52691

Reaction equation

3-methoxyphenylboronic acid

4,5-dimethoxy-2-bromobenzaldehyde

sodium carbonate

→

2-(3-methoxyphenyl)-4,5-dimethoxybenzaldehyde

Yield 98.0%

Solvents

toluene

ethanol

Conditions

Workup

1. 1
   Temperaturethe mixture was heated to reflux
2. 2
   Otherthe reaction was partitioned between water (150 ml) and ethyl acetate (300 ml)
3. 3
   WashThe organic layer was washed with saturated aqueous sodium bicarbonate (150 ml) and brine (150 ml)
4. 4
   Dryingdried over magnesium sulfate
5. 5
   Concentrationconcentrated

Procedure

Tetrakis(triphenylphosphine)palladium(0) (0.36 g) was added to a solution of 4,5-dimethoxy-2-bromobenzaldehyde (2.5 g) in toluene (20 ml) and ethanol (20 ml), followed by addition of 2M aqueous sodium carbonate (20 ml). To this mixture was added 3-methoxyphenylboronic acid (1.7 g), and the mixture was heated to reflux. After 1 hour, the reaction was partitioned between water (150 ml) and ethyl acetate (300 ml). The organic layer was washed with saturated aqueous sodium bicarbonate (150 ml) and brine (150 ml), dried over magnesium sulfate and concentrated. Chromatography (silica, 20-30-40% ethyl acetate/hexanes) afforded 2.7 g (98%) of 2-(3-methoxyphenyl)-4,5-dimethoxybenzaldehyde as a yellow oil which solidified upon standing.

Source