Boron tribromide → 4-[(Biphenyl-4-carbonyl)-amino]-2-hydroxy benzoic acid

Participants

Reaction Steps

A solution of 4-[(biphenyl-4-carbonyl)amino]-2-methoxy benzoic acid (2.78 g; 8 mmol) in CHCl3 (175 mL) was cooled until it became cloudy (approx. 40° C.) and BBr3 (1.5 mL; 16 mmol) was added over 2 minutes. The mixture was allowed to warm slightly with stirring for 2 hours after which time another 1.5 mL BBr3 (16 mmol) was added and the reaction mixture was left to warm to room temperature overnight. The resulting slurry was added brine (50 mL) and the organic solvent was removed in vacuo. The resulting solid was Isolated by filtration, washed with H2O, air dried, refluxed in 99% EtOH (100 mL), cooled and filtered to yield 2.2 g (82%) of a white solid. Mp. 266° C. (decomposes).

Provenance & Evidence