Liquid-phase and biphasic (CCl4/concd hydrochloric acid) chlorination of some iodoarenes to form the corresponding (dichloroiodo)arenes, prepared in 60–100% crude yields, are reported; dichlorine is produced as follows: Na2S2O8 + 2 HCl (conc. aq.) → Cl2 + 2 NaHSO4.
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The nuclear and/or side-chain chlorination of benzene, naphthalene, 1,4-xylene, mesitylene, anisole, phenol and chlorobenzene with Na2S2O8 as the oxidant was studied in 4:1 (v/v) acetonitrile–water solution containing hydrochloric acid. CuCl2 was found to be an efficient scavenger for the cation radicals and, if used in the presence of excess of Cl- ion and S2O82-, provides a useful process for the nuclear chlorination of activated aromatics, see: LedwichA., and RusselP. J., J. Chem. Soc., Perkin Trans. II, 1975, 1503. Later, also Swedish chemists studied the same oxidative chlorination of benzene, toluene, three xylenes, mesitylene, and naphthalene by Na2S2O8 / LiCl in aq. acetonitrile, in the presence or absence of CuCl2, see L. Eberson and L.-G. Wistrand, Liebigs Ann. Chem. 1976, 1777.
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