6-Methoxyquinoline → 5-Bromo-6-methoxyquinoline

Participants

Reaction Steps

To a solution of 6-methoxyquinoline (5 g, 31.4 mmol) in acetic acid (50 mL) was slowly added Br2 neat (1.62 mL, 31.4 mmol). The reaction mixture was stirred at ambient temperature for 1 hour and then poured onto ice. Saturated aqueous sodium bisulfite was added, and the resulting slurry was extracted into EtOAc (2×200 mL). The organic fractions were combined, dried over Na2SO4, concentrated, and purified by column chromatography (5% MeOH/CH2Cl2) affording 4.39 g of the title compound as the acetate salt. The free base was prepared by washing the salt with 1 N NaOH (50 mL) and H2O (100 mL) and extracting into CH2Cl2 (200 mL). The organic fractions were concentrated affording 3.89 g (52%) of the title compound as a pink solid.

Provenance & Evidence