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A Convenient Synthesis of 7-Halo-1-indanones and 8-Halo-1-tetralones

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journal contribution
posted on 26.12.2003 by Phong Nguyen, Evelyn Corpuz, Todd M. Heidelbaugh, Ken Chow, Michael E. Garst
A regioselective oxidation of N-indan-4-yl-acetamide or N-(5,6,7,8-tetrahydronaphthalen-1-yl)acetamide with potassium permanganate followed by acidic hydrolysis gave 7-aminoindan-1-one or 8-aminotetral-1-one in good yield. The amino ketones were converted to the corresponding 7-haloindanone or the 8-halotetralone. Another method to prepare 7-haloindan-1-ones was completed by a cyclization of 3-chloro-1-(2-halophenyl)propan-1-one under Friedel−Crafts conditions to produce the product in gram quantity.