Potassium Hydroxide → 5-Bromo-2-methoxypyridine

Participants

Reaction Steps

To a solution of KOH (4.2 g, 0.075 mol) in water (750 mL) was added 2-methoxypyridine 16-1 (16.4 g, 0.15 mol) followed by a dropwise addition of bromine (24 g, 0.15 mol) in 1N aqueous KBr (750 mL) and the resulting solution was stirred at room temperature for 5 hr. Solid NaHCO3 was added until basic and the solution was extracted with CHCl3 (3×500 mL). The organic layer was washed with 10% NaHSO3, then brine, dried over Na2SO4, filtered, and the solvent removed in vacuo. The resulting dark brown oil was predominantly the desired compound 16-2 and was used as such in the next step.

Provenance & Evidence