A convenient synthesis of 7-halo-1-indanones and 8-halo-1-tetralones

J Org Chem. 2003 Dec 26;68(26):10195-8. doi: 10.1021/jo035289s.

Abstract

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.

MeSH terms

  • Hydrocarbons, Halogenated / chemical synthesis*
  • Indans / chemical synthesis*
  • Tetralones / chemical synthesis*

Substances

  • Hydrocarbons, Halogenated
  • Indans
  • Tetralones