Nitration of aryl halides

An interesting case is provided by the nitration of aryl halides where the effect of the halogen is to deactivate the aromatic nucleus (by the -I effect) but to direct the incoming nitronium ion to the ortho and para positions as a result of the mesomeric interaction of the halogen lone electron pair with the charge developed in the corresponding intermediates [e.g. (5), in the formation of p-bromonitrobenzene from bromobenzene, Expt 6.20],... 

In 2005, Saito et al. described the nitration of aryl halides catalyzed by 5% of copper bronze, using tetra-n-butylammonium nitrite as a nitrating agent and the DMEDA L26 as ligand [264]. This efficient system, which offers the aromatic nitro compounds in fair to excellent yields, constitutes an interesting alternative to the traditional more drastic industrial method involving the electrophilic nitration of aromatic compounds (Scheme 22). 

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See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ , , , ]

See also in sourсe #XX -- [ ]

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