Bromine → 5-Bromo-2,3-dimethoxypyridine

Temperature

25 °C

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.

1. customThe reaction mixture was quenched with solid Na2SO3 (˜10 g)
2. extractionthe aqueous phase was extracted with dichloromethane (3×100 mL)
3. dry with materialThe organic phase was dried over magnesium sulfate
4. concentrationconcentrated
5. customThe residue was purified via normal phase chromatography (0 to 20% EtOAc in hexanes, silica)

ORD record

ord-431d313e6da14df89a9f365c33d5ca1f

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592457B2