Ethyl bromoacetate → Ethyl 2-(2-acetyl-4-bromophenoxy)acetate

Participants

Reaction Steps

To a solution of 1-(5-bromo-2-hydroxyphenyl)ethan-1-one (10 g, 46.50 mmol) in N,N-dimethylformamide (80 mL) was added sodium hydroxide (2.23 g, 92.92 mmol) and then stirred for 1 hour at room temperature. Ethyl 2-bromoacetate (8.24 g, 49.34 mmol) was added dropwise and stirred overnight at room temperature. The reaction mixture was quenched by the addition of water (200 mL), adjusted to pH 5 with HCl (3N), extracted with ethyl acetate (50 mL×3), dried over anhydrous sodium sulfate, and concentrated under vacuum to give a residue which was purified by silica gel chromatography (5% ethyl acetate in petroleum ether) to afford ethyl 2-(2-acetyl-4-bromophenoxy)acetate as a light yellow oil (8.9 g, 64%).

Provenance & Evidence