[Mg].II.Br[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]=[C:12]([F:14])[F:13])[CH:6]=1.[CH:15](N1CCCCC1)=[O:16].Cl>O1CCCC1>[F:13][C:12]([F:14])=[CH:11][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[CH:15]=[O:16]To a mixture of 0.67 g of magnesium and 10 ml of tetrahydrofuran was added a catalytic amount of iodine, and added dropwise a solution of 6.0 g of 1-bromo-3-(2,2-difluoroethenyl)benzene in 20 ml of tetrahydrofuran at 55° C. After stirred at room temperature for 15 minutes, a solution of 3.98 g of 1-formylpiperidine in 5 ml of tetrahydrofuran was added dropwise. This was heated under reflux for 15 minutes, and ice water and 10% hydrochloric acid were added, followed by extraction with t-butyl methyl ether. The organic layer was washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate and then concentrated. The resulting residue was subjected to silica gel column chromatography to obtained 1.13 g of oily 3-(2,2-difluoroethenyl)benzaldehyde [Compound No. (1)].
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