Sulfuric Acid → 3-Bromo-4-chloro-2,6-dimethylpyridine

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Reaction Steps

4-chloro-2,6-dimethylpyridine (1.5 g) was added to a mixed solvent of trifluoroacetic acid (3 mL) and concentrated sulfuric acid (6 mL). NBS (22 g) was added to the solution, and the mixture was stirred at room temperature for 12 hours. A 5 N aqueous sodium hydroxide solution was added to the reaction mixture, followed by separation with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous magnesium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%) to give the title compound (500 mg).

Provenance & Evidence