Carbon tetrabromide → Ethyl 5-(bromomethyl)-1,2-oxazole-3-carboxylate

Participants

Reaction Steps

Carbon tetrabromide (5.44 g; 16.39 mmol) was added to the solution of triphenylphosphine (4.34 g, 16.39 mmol) in THF (50 mL) and the resulting mixture was stirred at room temperature for 15 min. To this green suspension was added a solution of ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate (1.87 g, 10.93 mmol) in THF (10 mL) and the resulting reaction mixture was stirred overnight at room temperature. The solid material was removed by filtration. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel (eluent: 15 to 100% dichloromethane in heptane) to afford 1.73 g (68%) of ethyl 5-(bromomethyl)isoxazole-3-carboxylate as a solid.

Provenance & Evidence