FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9][C:8]=1[O:15][CH3:16])(=O)=O.CCOC(C)=O.[CH3:25][N:26](C=O)C>[C-]#N.[Zn+2].[C-]#N>[CH:13]([C:10]1[CH:11]=[CH:12][C:7]([C:25]#[N:26])=[C:8]([O:15][CH3:16])[CH:9]=1)=[O:14]A mixture of 4-formyl-2-methoxyphenyl trifluoromethanesulfonate (37.0 g, 130 mmol), zinc cyanide (61.0 g, 521 mmol) and tetrakis triphenylphosphine palladium (0) (22.6 g, 19.5 mmol) in DMF (300 mL) were stirred at 110° C. for 8 h. EtOAc was added to the reaction mixture and the organic layer was washed two times with water, dried, filtered and concentrated. The crude product was then purified by column chromatography (silica gel, ethylacetate/hexanes 3:7) which afforded 4-formyl-2-methoxybenzonitrile.
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