Bromination of tetralin. Short and efficient synthesis of 1,4-dibromonaphthalene

Çakmak O., Kahveci I., Demirtaş İ., Hökelek T., Smith K.

Collection of Czechoslovak Chemical Communications, vol.65, no.11, pp.1791-1804, 2000 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 65 Issue: 11
  • Publication Date: 2000
  • Doi Number: 10.1135/cccc20001791
  • Journal Name: Collection of Czechoslovak Chemical Communications
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1791-1804
  • Keywords: Aromatic nucleophilic substitution, Bromination, Bromine, Halogenation, Naphthalenes, Photobromination, Tetralin
  • Ondokuz Mayıs University Affiliated: No

Abstract

High-temperature bromination of tetralin (1,2,3,4-tetrahydronaphthalene) with bromine resulted in benzylic biomination to give 1,4-dibromo-1,2,3,4-tetrahydronaphthalene (4) as a major product and several secondary products. Photolytic bromination of tetralin and subsequent double dehydrobromination of 1,1,4,4-tetrabromo-1,2,3,4-tetrahydronaphthalene (10) gave 1,4-dibromonaphthalene (11) as the sole product in a high yield. 1,4-Dibromonaphthalene is efficiently converted to the corresponding methoxy (12 and 13) and cyano (14 and 15) derivatives of naphthalene.