Bromine → 3-Bromo-5-chloro-2-methoxypyridine

To a stirred suspension of 2.5 g of anhydrous sodium acetate in 10 ml of acetic acid was added 4.3 g of 5-chloro-2-methoxypyridine followed by a solution of 3.1 ml of bromine in 10 ml of acetic acid. The mixture was warmed to 80° C. for 6 hours and then allowed to cool and stirred at 23° C. for 64 hours. It was then partitioned between ether and water and the resulting ether layer was washed with aqueous 1N sodium hydroxide solution and then with aqueous 5% sodium bisulfite solution, dried over potassium carbonate and concentrated at reduced pressure to leave a residual brown solid. This residue was bulb-to-bulb distilled with the material distilling at 140°-150° C. at 20 torr collected to give 3-bromo-5-chloro-2-methoxypyridine as a solid melting at about 45°-47.5° C.