A Simple and Efficient Method for the Synthesis of ۲,۳,۵,۶-Tetrachloro-۴- iodopyridine, and its Reactivity Toward Hard and Soft Nucleophiles

۲,۳,۵,۶-tetrachloro-۴-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 ۲,۳,۵,۶-tetrachloro-۴-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, ۱H NMR, and ۱۳C NMR spectroscopy, confirmed the structures of all the compounds.

Keywords:

Pentachloropyridine , Tetrachloro-۴-iodopyridine , Regiochemistry , Microwave , Heterocycle