%0 Journal Article %T A Simple and Efficient Method for the Synthesis of 2,3,5,6-Tetrachloro-4- iodopyridine, and its Reactivity Toward Hard and Soft Nucleophiles %J Organic Chemistry Research %I Iranian Chemical Society %Z 2383-242X %A Ranjbar-Karimi*, Reza %A Davoodian, Tayebeh %A Poorfreidoni, Alireza %A Mehrabi, Hossein %D 2019 %\ 09/01/2019 %V 5 %N 1 %P 73-79 %! A Simple and Efficient Method for the Synthesis of 2,3,5,6-Tetrachloro-4- iodopyridine, and its Reactivity Toward Hard and Soft Nucleophiles %K Pentachloropyridine %K Tetrachloro-4-iodopyridine %K Regiochemistry %K Microwave %K Heterocycle %R 10.22036/org.chem.2018.130893.1143 %X 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. %U https://www.orgchemres.org/article_76917_b897989d53918787d4786406934687af.pdf