Boron tribromide → 6-Methoxyquinolin-8-ol

Participants

Reaction Conditions

Reaction Steps

To a −25° C. solution of 3.0 g (15.9 mmol) 6,8-dimethoxyquinoline and 160 mL CH2Cl2 is added 16 mL (15.9 mmol) of 1M BBr3 in CH2Cl2. After stirring for 2 h at −25° C., the reaction mixture is quenched with 300 mL of H2O, the layers separated in a separatory funnel, and the aqueous extracted with CH2Cl2 (2×100 mL). The combined organics are washed with 1×100 mL H2O, 1×100 mL brine, dried over MgSO4, filtered, and the volatiles are evaporated. Flash chromatography on SiO2, eluting with 3/1 EtOAc/hexanes containing 10% MeOH, gives 0.96 g (5.48 mmol, a 34% yield) of the title compound as an tan solid. MS (ES) m/z 176 (MH)+.

Provenance & Evidence