Polybromination of naphthalene using bromine over a montmorillonite clay and regioselective synthesis of 2,6-dibromonaphthalene

Smith, Keith, Al-Khalaf, Alaa K. H., Akar, Kıymet Berkil, Kariuki, Benson M. ORCID: https://orcid.org/0000-0002-8658-3897 and El-Hiti, Gamal A. 2022. Polybromination of naphthalene using bromine over a montmorillonite clay and regioselective synthesis of 2,6-dibromonaphthalene. ARKIVOC 2022 (5) , pp. 46-59. 10.24820/ark.5550190.p011.717

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Abstract

Reaction of naphthalene and bromine (three mole equivalents) at room temperature gave 1,4,6- tribromonaphthalene (66%) along with 1,4-dibromonaphthalene (8%) and 1,5-dibromonaphthalene (10%). Crystallization of the crude product gave pure 1,4,6-tribromonaphthalene in 50% yield. Bromination of naphthalene using four mole equivalents of bromine over KSF clay gave 1,2,4,6-tetrabromonaphthalene (92%) along with 1,3,5,7-tetrabromonaphthalene (5%). Crystallization of the crude products gave 1,2,4,6- tetrabromonaphthalene, a previously unreported compound, and 1,3,5,7-tetrabromonaphthalene in 70% and 4% isolated yields, respectively. Proto-debromination of the crude tetrabromination product, using two mole equivalents of n-butyllithium at a low temperature for a short reaction time, gave 2,6-dibromonaphthalene regioselectively in 82% yield after crystallization.

Item Type:	Article
Date Type:	Published Online
Status:	Published
Schools:	Chemistry
Additional Information:	This paper is an open access article distributed under the terms of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/)
Publisher:	ARKAT USA
ISSN:	1551-7012
Date of First Compliant Deposit:	4 May 2022
Date of Acceptance:	10 March 2022
Last Modified:	12 May 2023 23:10
URI:	https://orca.cardiff.ac.uk/id/eprint/149515

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