[F:1][C:2]1[CH:9]=[CH:8][C:5](C#N)=[CH:4][N:3]=1.C[Mg]Br.C(=O)(O)[O-].[Na+].CC[O:20][CH2:21][CH3:22]>C1COCC1>[F:1][C:2]1[N:3]=[CH:4][C:5]([C:21](=[O:20])[CH3:22])=[CH:8][CH:9]=1
To a solution of 6-fluoronicotinonitrile (5.00 g, 41.0 mmol) in THF (50 mL) was added 1 N methylmagnesium bromide (16.4 mL, 49.1 mmol) in THF at 0° C. After addition, the mixture was warmed to ambient temperature and stirred at ambient temperature for 4 hours. Saturated sodium bicarbonate solution (50 mL) and ether (100 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate) to give 1-(6-fluoropyridin-3-yl)ethanone (0.85 g, 14.9%) as solid.
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