Chloroform → 3-Bromo-6-methoxy-2-methylpyridine

A mixture of 5-bromo-6-methyl-1H-pyridin-2-one (5.5 g, 29 mmol), silver carbonate (10.89 g, 39 mmol), iodomethane (13.6 mL, 217 mmol) and chloroform (115 mL) is stirred overnight in the dark at room temperature. Triethylamine (10 mL) is added and stirring continued for 1.5 hr. The reaction mixture is filtered through a pad of Hi-Flo and the filtrate is washed with water (100 mL), dried, filtered and concentrated. The residue is purified by filtration through a pad of silica gel washing with cyclohexane-20% ethyl acetate. The solvent is concentrated to afford 3-bromo-6-methoxy-2-methylpyridine (3.7 g, 63% yield) as an oil. LC/MS RT 3.76 min; MS m/e=202/204 (M); NMR (CDCl3) 7.6 (1H, d), 6.43 (1H, d), 3.89 (3H, s), 2.57 (3H, s).

1. stirringstirring
2. waitcontinued for 1.5 hr
3. filtrationThe reaction mixture is filtered through a pad of Hi-Flo
4. washthe filtrate is washed with water (100 mL)
5. customdried
6. filtrationfiltered
7. concentrationconcentrated
8. filtrationThe residue is purified by filtration through a pad of silica gel washing with cyclohexane-20% ethyl acetate
9. concentrationThe solvent is concentrated

ORD record

ord-9710f8b4226d407eb8f59d8ce57d0962

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173682B2