[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([I:14])[CH:13]=1)[C:8]([NH2:10])=O)=[O:4]>S(Cl)(Cl)=O>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:13]=[C:12]([I:14])[CH:11]=[C:7]([C:8]#[N:10])[CH:6]=1A mixture of 3-methoxycarbonyl-5-iodobenzamide (2.5 g, 8.2 mmol) in thionyl chloride (2 mL) was heated for 2 hours at 90° C. The reaction mixture was cooled and concentrated in vacuo. Silica gel chromatography afforded 670 mg (29%) of methyl-3-cyano-5-iodobenzoate, as a white solid.
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