Gao Wen-ta
2014
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Journal
Chemical Research and Application
Abstract
5-Methyl-,chloro,and bromo-substituted 2-hydroxy-acetophenones(2a-c) were synthesized in good yields of 77.3%-80.4%,involving the acetylation reaction of the respective 4-methyl-,chloro,and bromo-phenols(1a-c) with acetic anhydride followed by Fries rearrangement in the presence of BF3·2HAc as catalyst under solvent-free condition.3,5-Dihalo-substituted 2-hydroxy-acetophenones(4a-c) were obtained in the yields of 61.8-92.4% by the halogenation reaction of 2-hydroxy-acetophenone(3)with N-halosuccinimide using PEG-400 as solvent at room temperature.The nitration of 2-hydroxy-acetophenone(3) with a green nitrating agent of cerium ammonium nitrate(CAN) was also investigated,affording two products 3-nitro-and 5-nitro-substituted 2-hydroxy-acetophenones(5a,b) in 29.8% and 63.9% yield,respectively.Our developed experimental procedures for the preparation of the 2-hydroxy-acetophenone derivatives 2a-c,4a-c,and 5a,b are characterized by mild conditions,simple work-up,and environmental benefits of the reaction medium,and thus could be used as a useful and green alternative approach to previously reported methods.