Sodium Hydroxide → 4-Bromo-2-ethylpyridine

Participants

Reaction Conditions

Reaction Steps

4-Amino-2-ethylpyridine (18 g) was dissolved with warming in 48 ml of 48% hydrogen bromide. The solution was cooled to 0° C. and 15 ml of bromine was added dropwise followed by a solution of 25.4 g of sodium nitrite in 37 ml of water over 1/2 hour while maintaining the temperature below 5° C. The mixture was allowed to warm to room temperature over 2 hours and was then poured onto ice and made alkaline with 35% sodium hydroxide. The aqueous mixture was extracted three times with 200 ml of methylene chloride, the extract was concentrated and the residue was taken up in diethyl ether. The ether solution was dried over magnesium sulfate and concentrated in vacuo at below 40° C. to give, after chromatography (silica gel; 70:30 hexane-ether), 4.1 g of the title compound as an orange oil.

Provenance & Evidence