Hydrogen Bromide → 2,5-Dibromo-4-propylpyridine

Participants

Reaction Conditions

Reaction Steps

5-Bromo-4-propylpyridine-2-amine (5.67 g, 26.3 mmol) was added 48% hydrogen bromide (21 mL) at 10° C. The mixture was added bromine (4.0 mL) under ice-cold conditions, and added dropwise with an aqueous solution (4.5 mL) of sodium nitrite (4.54 g) at −10° C. The mixture was stirred at −10° C. for 0.5 hours, then added 1N aqueous solution of sodium hydroxide (10 mL), and stirred at room temperature for 2 hours. The reaction solution was added water, extracted with diethylether. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (diethylether), and the title compound (6.96 g (yield 95%)) was obtained as a brown oil.

Provenance & Evidence