Collect. Czech. Chem. Commun. 2000, 65, 1791-1804

Bromination of Tetralin. Short and Efficient Synthesis of 1,4-Dibromonaphthalene

Osman Çakmaka,*, Ismail Kahvecia, Íbrahim Demirtaşa, Tuncer Hökelekb and Keith Smithc

a Gaziosmanpaşa University, Faculty of Science, Department of Chemistry, 60100 Tokat, Turkey
b Hacettepe University, Department of Physics, 06532 Beytepe, Ankara, Turkey
c Department of Chemistry, University of Wales Swansea, Swansea SA2 8PP, U.K.


High-temperature bromination of tetralin (1,2,3,4-tetrahydronaphthalene) with bromine resulted in benzylic bromination 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.

Keywords: Bromine; Photobromination; Bromination; Halogenation; Naphthalenes; Tetralin; Aromatic nucleophilic substitution.

References: 55 live references.