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

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.