Methanol → (2-Bromopyridin-3-yl)methanol

To a 2 L round bottom flask (fitted with stir bar, under nitrogen and at 0° C.) containing 2-bromo-3-pyridine-carboxaldehyde (22.15 g, 119.08 mmol) and methanol (200 mL), is added sodium borohydride (1.35 g, 35.72 mmol) in three portions. After 1 h at 0° C. water (200 mL) is added and the reaction is concentrated under reduced pressure to remove the methanol. The resulting residue is dissolved in ethyl acetate and washed with water (200 mL). The organic extraction is washed with brine, dried over magnesium sulfate, filtered and concentrated to afford 22 g of (2-bromo-3-pyridyl)methanol as a white solid. MS (m/z): 188 (M+1), 190 (M+3).

1. customTo a 2 L round bottom flask (fitted with stir bar, under nitrogen and at 0° C.)
2. concentrationthe reaction is concentrated under reduced pressure
3. customto remove the methanol
4. dissolutionThe resulting residue is dissolved in ethyl acetate
5. washwashed with water (200 mL)
6. extractionThe organic extraction
7. washis washed with brine
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-f24dc3be46914fefa9d8ec3773f09625

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08232289B2