Boron tribromide → 6-Hydroxy-2-(3-nitrophenyl)quinazolin-4(1H)-one

Participants

Reaction Conditions

Reaction Steps

To a suspension of 6-methoxy-2-(3-nitrophenyl)quinazolin-4(3H)-one (3.90 g, 13.1 mmol), in CH2Cl2 (30 mL) cooled to −78° C. under an atmosphere of N2 was added BBr3 as a 1.0M solution in CH2Cl2 (20 mL, 20.0 mmol). The resulting mixture was stirred at −78° C. for 1 h, then allowed to warm to RT upon which it was stirred for a further 3 h. The mixture was re-cooled to −78° C. and stirred overnight. The reaction was quenched by the addition of EtOH (60 mL) and allowed to warm to RT. Stirring was continued for 1 h at RT, upon which a precipitate formed. Sat. NaHCO3 solution was added and the yellow solid was collected via filtration and washed with Et2O and EtOH and dried under vacuum to give 6-hydroxy-2-(3-nitrophenyl)quinazolin-4(3H)-one (2.96 g, 10.5 mmol, 80%). HPLC retention time 5.588 min.

Provenance & Evidence