N-bromobutanimide → 5-((4-Bromo-2-chlorophenyl)amino)-4-fluorobenzo[d]oxazole-6-carboxylic acid

Participants

Reaction Steps

To a solution of 5-((2-chlorophenyl)amino)-4-fluorobenzo[d]oxazole-6-carboxylic acid (12.31 g, 40.14 mmol) in DMF (100 mL) was added NBS (7.86 g, 44.15 mmol). After stirring for 4 h at ambient temperature, the reaction was quenched by water and the precipitate was filtered. The crude product was purified by column chromatography on silica gel (CH2Cl2/MeOH, 50:1, v/v) and gave the desired product (pale brown solid, 10.82 g, 69.9% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.08 (s, 1H), 9.42 (s, 1H), 8.96 (s, 1H), 8.27 (s, 1H), 7.82 (d, J=12.0 Hz, 1H), 7.37 (m, 1H), 6.65 (m, 1H).

Provenance & Evidence