Sodium borohydride → (2-Bromopyridin-3-yl)methanol

To a solution of 2-bromo-3-formylpyridine (2.51 g) in methanol (40 ml) was added, at room temperature, sodium borohydride (255 mg). The mixture was stirred for 15 minutes at the same temperature. The reaction mixture was concentrated, to which was added water, followed by subjecting the mixture to extraction. The extract solution was washed with a saturated aqueous saline solution, dried (anhydrous sodium sulfate), which was then concentrated to afford 2-bromo-3-hydroxymethylpyridine (2.40 g). To a mixture of this compound (2.40 g), iodomethane (5.44 g) and DMF (25 ml) was added, at room temperature, 60% sodium hydride (613 mg), and the mixture was stirred for 30 minutes at the same temperature. To the reaction mixture was poured water, which was subjected to extraction with ethyl acetate. The extract solution was washed with water, which was dried (anhydrous sodium sulfate), followed by concentration. The residue was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane) to afford 2-bromo-3-methoxymethylpyridine (2.34 g) as a yellow liquid product.

1. concentrationThe reaction mixture was concentrated, to which
2. additionwas added water
3. extractionto extraction
4. washThe extract solution was washed with a saturated aqueous saline solution
5. dry with materialdried (anhydrous sodium sulfate), which
6. concentrationwas then concentrated

ORD record

ord-0a53d5e2eb0f4f9ba592cd3625e14f6d

Source dataset

uspto-grants-1998_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05716971