Water → 3,4-Difluoro-5-formylbenzonitrile
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Br[C:2]1[CH:3]=[C:4]([F:11])[C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[Cu](C#N)[C:13]#[N:14].C(OCC)(=O)C.O>CN1CCCC1=O>[F:11][C:4]1[CH:3]=[C:2]([CH:9]=[C:6]([CH:7]=[O:8])[C:5]=1[F:10])[C:13]#[N:14]Br[C:2]1[CH:3]=[C:4]([F:11])[C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[Cu](C#N)[C:13]#[N:14].C(OCC)(=O)C.O>CN1CCCC1=O>[F:11][C:4]1[CH:3]=[C:2]([CH:9]=[C:6]([CH:7]=[O:8])[C:5]=1[F:10])[C:13]#[N:14]To a solution of 10.0 g of 5-bromo-2,3-difluorobenzaldehyde in 40.0 mL of 1-methyl-2-pyrrolidone was added 4.26 g of copper cyanide (I) at room temperature and stirred at 170° C. for 8 hours. Adding ethyl acetate and water, the solution was stirred, and insoluble substances were filtered out through celite. The organic layer of filtrate was washed successively with saturated aqueous ammonium chloride, water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:20), to afford 2.64 g of the title compound as colorless crystals.
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