Spectroscopic and structural study of flobufen

Alexandr Jegorov
Petr Sedmera, Institute of Microbiology of the Academy of Sciences of the Czech Republic
Vladimír Havlíček, Institute of Microbiology of the Academy of Sciences of the Czech Republic
Michal Hušák, University of Chemistry and Technology, Prague
Svetlana Pakhomova, University of Chemistry and Technology, Prague
Bohumil Kratochvíl, University of Chemistry and Technology, Prague
Miroslav Kuchař, Research Institute of Pharmacy and Biochemistry, Prague
Petr Bulej

Abstract

Flobufen, 4-(2′,4′-difluorobiphenyl-4-yl)-2-methyl-4-oxobutanoicacid, and its 3-methyl isomer have been obtained by the Friedel-Crafts reaction of 2,4-difluorobiphenyl with itaconic or citraconic anhydride, respectively, followed by hydrogenation of the products. The structures of both compounds have been elucidated by mass spectrometry and 1H, 13C and 19F NMR spectroscopy. The structure of flobufen has been confirmed by a single-crystal X-ray study. © 1995 Elsevier Science S.A. All rights reserved.