Hydrogen Bromide → 5-Bromo-4,6-dimethylpicolinonitrile

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Reaction Steps

5-amino-4,6-dimethylpicolinonitrile (390 mg) was added to aqueous hydrogen bromide (2.9 mL). Bromine (164 μl) and sodium nitrite (467 mg) were added to the solution at 0° C. The solution was warmed to room temperature and stirred for four 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 using 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, 0% to 30%) to give the title compound (300 mg).

Provenance & Evidence