[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13](I)[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[CH3:16][N:17](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([C:16]#[N:17])[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]A mixture of t-butyl 3-bromo-5-iodobenzoate (1.91 g, 5 mmol), zinc cyanide (585 mg, 5 mmol), and tetrakis(triphenylphosphine)palladium(0) (300 mg, 5 mol %) in dimethylformamide (20 ml) was heated at 80° C. for 2 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (20 ml) and washed with water and brine. The organic phase was dried and evaporated. Chromatography with ethyl acetate/hexane (1:4) gave the title compound as a colourless oil (1.02 g, 73%).
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