3-Bromo-2-chloro-5-methylpyridine → 3-Bromo-2-methoxy-5-methylpyridine

Temperature

65 °C

To a solution of 3-bromo-2-chloro-5-methylpyridine (5 g, 24.2 mmol) in MeOH (80 mL) was added a solution of sodium methoxide 5.4M in MeOH (25 mL, 135 mmol) and the mixture was stirred at 65° C. for 32 h. The resulting suspension was filtered and the mother liquor was concentrated. Et2O and H2O were added and the phases were separated. The organic layer was washed with H2O and brine, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (heptane/EtOAc: 90:10→0:100) to afford the title compound. tR: 1.03 min (LC-MS 2).

1. filtrationThe resulting suspension was filtered
2. concentrationthe mother liquor was concentrated
3. additionEt2O and H2O were added
4. customthe phases were separated
5. washThe organic layer was washed with H2O and brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by flash chromatography (heptane/EtOAc: 90:10→0:100)

ORD record

ord-7bb6e1d214454353b99874a7d07d41b1

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815926B2