Carbon tetrabromide → 4-(2,2-Dibromo-vinyl)-5-methyl-3-phenyl-isoxazole

Participants

Reaction Steps

To a stirred solution of 5-methyl-3-phenyl-isoxazole-4-carbaldehyde (5.20 g, 27.8 mmol) was added tetrabromomethane (12.9 g, 38.9 mmol) and then triphenylphosphine (14.57 g, 55.5 mmol) and the resulting mixture stirred under argon for 2 h at 0° C. The solution was concentrated to approximately 90 mL and the resulting precipitate filtered, washed with dichloromethane and discarded. This was repeated until the majority of the triphenylphospine oxide and bromide was removed. Purification by chromatography (silica, heptane:ethyl acetate 9:1 to 2:3) afforded the title compound (7.9 g, 83%) which was obtained as a colorless oil. MS: m/e=344.0 [M+H]+.

Provenance & Evidence