反应详情

To a solution of 5-bromo-2-fluoronicotinaldehyde (10 g, 49 mmol) in THF (100 mL) at −78° C. was added dropwise methylmagnesium bromide (3.0 M solution in diethyl ether, 24.5 mL, 73.5 mmol). After the addition, the reaction was warmed to room temperature and stirred for 17 h. The mixture was carefully quenched with saturated ammonium chloride and extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 0-10% EtOAc/hexanes) gave 1-(5-bromo-2-fluoropyridin-3-yl)ethanol (10.8 g, 49.1 mmol, 100% yield) as a yellow oil. LC/MS (ESI+) m/z=220 (M+H).

1. additionAfter the addition
2. customThe mixture was carefully quenched with saturated ammonium chloride
3. extractionextracted with EtOAc
4. washThe combined organic extracts were washed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customPurification by flash column chromatography on silica gel (eluted with 0-10% EtOAc/hexanes)