A convenient synthesis of 7-halo-1-indanones and 8-halo-1-tetralones.
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.
Nguyen
Phong
P
Allergan, Inc., 2525 Dupont Drive, Irvine, California 92623, USA.
Corpuz
Evelyn
E
Heidelbaugh
Todd M
TM
Chow
Ken
K
Garst
Michael E
ME
D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis*; D007189:Indans / Q000138:chemical synthesis*; D044024:Tetralones / Q000138:chemical synthesis*
D006846:Hydrocarbons, Halogenated; D007189:Indans; D044024:Tetralones