Bromination of 5-methoxyindane: Synthesis of new benzoindenone derivatives and ready access to 7H-Benzo[c]fluoren-7-one skeleton

TUTAR A., BERKİL AKAR K., Hark R. R., BALCI M.

SYNTHETIC COMMUNICATIONS, vol.38, no.9, pp.1333-1345, 2008 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 38 Issue: 9
  • Publication Date: 2008
  • Doi Number: 10.1080/00397910801916223
  • Journal Name: SYNTHETIC COMMUNICATIONS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1333-1345
  • Middle East Technical University Affiliated: No

Abstract

The photobromination of 5-methoxyindane and 5-methoxyindanone was studied at both high and low temperatures. 1,2,3-Tribromo-6-methoxyindene was easily synthesized by photolytic bromination of 5-methoxyindane at low temperature. 1,1,2,3-Tetrabromo-6-methoxyindene was obtained from the photobromination of 5-methoxyindan at 77 degrees C, which could then be easily converted to the 2,3-dibromo-6-methoxyindene by silver-supported hydrolysis. Photochemical bromination of 5-methoxy-1-indanone with N-bromosuccinimide (NBS) gave 3-bromo-6-methoxyindene, which upon thermolysis gave a benzo[c]fluorenone derivative.