Tetrahedron

Selective bromination of 1-bromonaphthalene: efficient synthesis of bromonaphthalene derivatives

O Cakmak, I Demirtas, HT Balaydin

Index: Cakmak, Osman; Demirtas, Ibrahim; Balaydin, Halis T Tetrahedron, 2002 , vol. 58, # 28 p. 5603 - 5609

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Citation Number: 32

Abstract

Selective and specific preparation methods are described for 1, 4-dibromonaphthalene, 1, 5- dibromonaphthalene and 1, 3, 5-tribromonaphthalene. The reaction of 1-bromonaphthalene and naphthalene with stoichometric quantities of bromine by using a minimum amount of solvent (methylene chloride) at− 30 and− 50° C smoothly affords 1, 4-dibromonaphthalene in 90% yield. Photobromination of 1-bromonaphthalene in CCl4 at− 30° C gives 1, 2, 3, 4, ...