Short and Selective Synthesis of 3,5-dibromoinden-1-one

Authors : Derya Celik, Ahmet Tutar, Ramazan Erenler

Pages : 1-4

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Publication Date : 2012-01-01

Article Type : Other

Abstract :Brominations of hydrocarbons are important processes in synthetic chemistry. Bromoindanes and bromoindenones are key intermediate for medicinally valuable compounds. Short and efficient synthesis of 3,5-dibromoinden-1-one is presented. 5-bromoindane-1-one 1 was treated with ethylene glycol to mask the ketone functional group to yield the cyclic ketal 2. Bromination of bromoindanecyclic ketal 2 with bromine in photochemical reaction apparatus while being irradiated with a projector lamp afforded the product which was treated with silica gel directly to remove the protective group afforded the corresponding 3,5-dibromoinden-1-one 3
Keywords : Photobromination, 5-bromoindanone ethylene ketal, 3, 5-dibromoinden-1-one, protecting group, radical mechanism