Hydrogen Bromide → 3-Bromo-2-chloro-4,6-dimethylpyridine

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Reaction Conditions

Reaction Steps

2-chloro-4,6-dimethylpyridin-3-amine (2.85 g) was dissolved in hydrobromic acid (15 mL, 48% aqueous solution), and the solution was cooled to 0° C. A solution of sodium nitrite (1.51 g) in water (2 mL) was slowly added dropwise to the solution, and the mixture was stirred at 0° C. for 15 minutes. A suspension of copper(I) bromide (4.18 g) in hydrobromic acid (5 mL, 48% aqueous solution) was added dropwise to the solution, and the mixture was stirred at 0° C. for 10 minutes and then at 60° C. for one hour. The reaction mixture was cooled to room temperature, followed by extraction with ethyl acetate. The organic layer was directly subjected to an NH-silica gel pad and eluted with ethyl acetate. The resulting solution was concentrated under reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate/n-heptane, 0% to 30%) to give the title compound (2.97 g).

Provenance & Evidence