Two Efficient Routes to m-Terphenyls from 1,3-Dichlorobenzenes

Akbar Saednya; Harold Hart

doi:10.1055/s-1996-4426

Synthesis 1996; 1996(12): 1455-1458
DOI: 10.1055/s-1996-4426

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Two Efficient Routes to m-Terphenyls from 1,3-Dichlorobenzenes

Akbar Saednya¹ , Harold Hart²

¹Faculty of Chemistry, University of Tabriz, Tabriz, Iran, Fax +98(41)340191
²Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA, FAX +1(517)3531793

Abstract

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In the first route 2,6-dichlorophenyllithium (5), prepared by direct lithiation of 1,3-dichlorobenzene, reacted with aryl Grignard reagents to give m-terphenyls in 57-93% yields (Table 1); the methodology was extended to substituted 1,3-dichlorobenzenes (i.e. 8 → 10). Also, reaction of 5 with MgCl₂ gave 2,6-dichlorophenylmagnesium chloride which, on warming, produced the self-capture product tetrachloro-m-terphenyl 7 in moderate yield. In the second route, reaction of 1,3-dichlorobenzene with excess of aryllithium in diethyl ether at room temperature gave the corresponding m-terphenyls in 59-94% yields (Table 2). Examples are given in which the aryllithium was prepared by three different routes (ArX+Li, ArX+t-BuLi, ArH+BuLi).

m-terphenyls - Grignard reagents - 1,3-dichlorobenzenes - aryllithium compounds

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