A Novel and Efficient Ceric Ammonium Nitrate Catalyzed Oxidative Nuclear Chlorination of Activated Aromatic Compounds by Acetyl Chloride

Abstract

A mild and efficient oxidative chlorination of activated aromatic compounds have been achieved in excellent yields using acetyl chloride in the presence of a catalytic amount of ceric ammonium nitrate at room temperature. However, chlorination failed to occur with deactivated aromatic rings.

Key words

ceric ammonium nitrate - nuclear chlorination - acetyl chloride

References

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15

General Procedure. To a stirred mixture of the aromatic substrate (1.5 mmol) and freshly distilled acetylchloride (1.52 mmol) in acetonitrile (10 mL), was added ceric ammonium nitrate (0.15 mmol) in one portion under N₂ at room temperature. The reaction mixture was allowed to stir for 7-8 h. After completion of the reaction (the progress of the reaction was monitored by TLC), the reaction mixture was diluted with diethyl ether (25 mL) and washed thoroughly with saturated aqueous NaHCO₃ solution (3 × 10 mL), brine (3 × 10 mL) and dried (Na₂SO₄). Volatiles were removed under reduced pressure and the residue obtained was purified by column chromatography over silica gel (2% ethyl acetate in light petroleum) to yield the pure chlorinated product.