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
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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 (Na2 SO4 ).
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