Boron tribromide → 8-bromo-5-hydroxy-4-(2-hydroxyethyl)quinolin-2(1H)-one

Participants

Reaction Steps

To a stirred solution of 8-bromo-4-(2-hydroxyethyl)-5-methoxyquinolin-2(1H)-one (2.7 g; 9.06 mmol) at −78° C. was added a solution of boron tribromide (1M in DCM) (55 ml; 55 mmol) dropwise. After 1 h the reaction mixture was allowed to warm up to room temperature and the stirring was carried out for 20 h. The reaction mixture was mixed with ice and water, the solid formed was isolated by filtration and dried over phosphorus pentoxide under reduced pressure to afford 1.56 g (45%) of 8-bromo-5-hydroxy-4-(2-hydroxyethyl)quinolin-2(1H)-one. The crude solid was used in the next step without further purification.

Provenance & Evidence