Ethyl Acetoacetate → Ethyl 4-bromo-3-oxobutanoate

Participants

Reaction Steps

A solution of bromine (436 g, 2.73 mol) in acetic acid (750 mL) was added to a solution of ethyl 3-oxobutanoate (355 g, 2.73 mol) in acetic acid (1000 mL). The mixture was stirred at room temperature for 72 hours and was concentrated under reduced pressure at 45° C. to remove the acetic acid. The residue was partitioned between methylene chloride (400 mL) and water (250 mL). The organic layer was washed with saturated sodium bicarbonate (2×300 mL), water (300 mL), brine (125 mL) and was dried over anhydrous magnesium sulfate. The solution was filtered and concentrated to give ethyl 4-bromo-3-oxobutanoate as a yellow oil (421 g).

Provenance & Evidence