Methyl iodide → 3-Bromo-2-methoxypyridine

Under an argon atmosphere, a mixture of 3-bromo-2-hydroxypyridine (3.49 g, 20 mmol), silver carbonate (3.67 g, 13.31 mmol), and iodomethane (1.5 mL, 24.1 mmol) in benzene (30 mL) was stirred in the dark at 40° C. to 50° C. for 24 hours, cooled in an ice bath, and filtered. The filtrate was washed once with 2% aqueous sodium bicarbonate and twice with water, dried (MgSO4), the benzene was evaporated at atmospheric pressure, and the residue was purified by flash chromatography (eluting with hexane/ethyl acetate, 2:1) to obtain the title compound (2.35 g, 12.5 mmol, 62%).

1. temperaturecooled in an ice bath
2. filtrationfiltered
3. washThe filtrate was washed once with 2% aqueous sodium bicarbonate and twice with water
4. dry with materialdried (MgSO4)
5. customthe benzene was evaporated at atmospheric pressure
6. customthe residue was purified by flash chromatography (eluting with hexane/ethyl acetate, 2:1)

ORD record

ord-ad0a923fc5134e3ead3d7adfab6b63fc

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07507744B2