A Simple and Efficient Method for the Synthesis of 2,3,5,6-Tetrachloro-4- iodopyridine, and its Reactivity Toward Hard and Soft Nucleophiles

Document Type : Research Paper


Department of Chemistry, Faculty of Science, Vali-e-Asr University, Rafsanjan 77176, Islamic Republic of Iran


2,3,5,6-tetrachloro-4-iodopyridine was successfully synthesized in one-step from the reaction of pentachloropyridine with sodium iodide using microwave irradiation. The reaction of O, N, and S centered nucleophiles with 2,3,5,6-tetrachloro-4-iodopyridine was studied in order to assess regiochemistry of aromatic nucleophilic substitution. Substitution occurs at the para position to ring nitrogen by S centered nucleophiles, while O and N centered nucleophiles substitution occurs at the ortho position of pyridine ring. IR, 1H NMR, and 13C NMR spectroscopy, confirmed the structures of all the compounds.