3-Bromoaniline → N-(3-Bromophenyl)-3-oxobutanimidic acid

Participants

Reaction Steps

To a heated (80° C., oil bath temperature) solution of 20.00 g (0.12M) of m-bromoaniline in 200 mL of dry toluene was added dropwise over a period of 30 min. 12 g (0.14M) of diketene in 100 mL of dry toluene. When the addition was completed, the reaction mixture was brought to reflux for 5 h. The toluene was then removed in vacuo, resulting in a yellow solid. Recrystallisation from toluene afforded 14.70 g (48%) of product as light pink crystals: mp 94°-95° C.

Provenance & Evidence