Pyridine → Methyl 3-(2-bromoacetamido)crotonate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 3-aminocrotonate (3.20 g, 27.79 mmol) and pyridine (2.64 g, 33.33 mmol) in CH2Cl2 (60 mL) was stirred at −20° C. for 20 min. To the mixture was added a solution of bromoacetyl bromide (5.61 g, 27.79 mmol) in CH2Cl2 (20 mL) dropwise. The mixture was stirred at rt for 2 h. The organic phase was washed with brine (100 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=5:1) to give the title compound as a reddish solid (0.99 g, 15%).

Provenance & Evidence