Bromine → 5-Bromo-2,3-dimethoxypyridine

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To a solution of 2,3-dimethoxypyridine (4-1, 2.5 g, 18.0 mmol, 1.0 equiv) in dichloromethane:saturated NaHCO3 (80 mL: 40 mL) at 0° C. was added bromine (0.93 mL, 18.0 mmol, 1.0 equiv) and the reaction mixture was stirred for 2 h at 25° C. The reaction mixture was quenched with solid Na2SO3 (˜10 g) and the aqueous phase was extracted with dichloromethane (3×100 mL). The organic phase was dried over magnesium sulfate and concentrated. The residue was purified via normal phase chromatography (0 to 20% EtOAc in hexanes, silica) to afford the desired product (4-2) as an oil after concentration. ESI+MS[M+H]+C7H8NO2 calc'd 218.0. found 218.0.

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