6-Bromo-3-pyridinecarboxaldehyde → HCID 86640808, compound

To a chilled (0° C.) solution of 6-bromo-pyridine-3-carboxaldehyde (15.0 g, 80.6 mmol) in a 1:1 mixture of ether-toluene (400 mL) was added a 2 M solution of ethyl magnesium chloride (40.0 mL, 80.0 mmol) in THF over a 15 minute period. The solution was stirred for 4 hours, and a more polar product was observed by TLC (ethyl acetate-hexanes 3:7). The mixture was diluted with saturated aqueous ammonium chloride (300 mL) and the organic phase separated. The aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine (2×50 mL), dried over magnesium sulfate, filtered and concentrated. The crude material was passed through a pad of silica gel eluting 0-100% dichloromethane in hexanes. The material from the pad was purified by silica gel chromatography eluting with a gradient of 2-15% ethyl acetate in hexanes to afford 1-(6-bromo-pyridin-3-yl)-propan-1-ol.

1. customthe organic phase separated
2. extractionThe aqueous layer was extracted with ethyl acetate (2×100 mL)
3. washThe combined organic layers were washed with brine (2×50 mL)
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe material from the pad was purified by silica gel chromatography
8. washeluting with a gradient of 2-15% ethyl acetate in hexanes

ORD record

ord-38452f3d761d4104a99cab4283e18eb8

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08263597B2