Reaction #1005928

Reaction equation

2-hydroxy-3-bromo- -4-methoxybenzaldehyde

t-butyldimethlsilyl chloride

→

2-(t-butyldimethylsilyl)-3-bromo-4-methoxy benzaldehyde

Yield 83.1%

Solvents

DMF

Conditions

Workup

1. 1
   ExtractionThe mixture was then extracted with ether (3×25 ml)
2. 2
   WashThe ethereal solution was washed with water (25 ml) and saturated NaHCO3 solution (2×15 ml)
3. 3
   OtherThe solvent evaporated

Procedure

Diiospropylethylamine (3.0 ml) was added to a stirred solution (under argon) of 2-hydroxy-3-bromo- -4-methoxybenzaldehyde (1.96, 8.5 mmole) in DMF (15 ml) followed by t-butyldimethlsilyl chloride (TBSCl, 1.91 g, 12.8 mmole). The reaction mixture was stirred at room temperature for 30 min and Ice (20 g) was added to the mixture. The mixture was then extracted with ether (3×25 ml). The ethereal solution was washed with water (25 ml) and saturated NaHCO3 solution (2×15 ml). The solvent evaporated to yield 2-(t-butyldimethylsilyl)-3-bromo-4-methoxy benzaldehyde as an oil (2.54 g, 7.06 mmole, 83.1%).

Source