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Current Organic Chemistry

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ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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Research Article

Modification for Nitration of Halo-substituted meso-Tetraarylporphyrins: A Convenient Scale-up in Small Amount of Solvent

Author(s): Mariusz Rosa, Maciej Malinowski and Stanisław Ostrowski*

Volume 27, Issue 11, 2023

Published on: 26 September, 2023

Page: [962 - 966] Pages: 5

DOI: 10.2174/1385272827666230717105700

Price: $65

Abstract

The synthesis of porphyrins with halogens and nitro groups in meso-aryl rings is described. Halo-substituted meso-tetraarylporphyrin derivatives in the reaction with sodium nitrite in trifluoroacetic acid at 40°C (or room temperature) afford 5-(4-nitroaryl)-10,15,20- triarylporphyrins. The above mono-nitro products bearing halogens on meso-aryl rings (F, Cl, Br) are difficult to obtain selectively. The method elaborated herein allows to synthesize them with reasonable yield (of up to 57%), and the reaction can be easily scaled-up. By this route, the preparation of valuable substrates for further transformation to highly substituted ‘synthetic porphyrins’ was presented.

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