Large-Scale Preparation of 1,1′-Ferrocenedicarboxylic
Acid, a Key Compound for the Synthesis of 1,1′-Disubstituted
Ferrocene Derivatives

Petrov, Alex R.; Jess, Kristof; Freytag, Matthias; Jones, Peter G.; Tamm, Matthias

doi:10.1021/om4004972.s003

Large-Scale Preparation of 1,1′-Ferrocenedicarboxylic Acid, a Key Compound for the Synthesis of 1,1′-Disubstituted Ferrocene Derivatives

journal contribution

posted on 2016-02-18, 13:30 authored by Alex R. Petrov, Kristof Jess, Matthias Freytag, Peter G. Jones, Matthias Tamm

Efficient and simple methods for the large-scale preparation of 1,1′-ferrocenedicarboxylic acid, fc(COOH)₂, involving the sodium salts of cyclopentadienecarboxylic methyl and ethyl esters, Na(C₅H₄COOR) (R = Me, Et), are presented. With fc(COOH)₂ at hand, the syntheses of various 1,1′-disubstituted compounds of the type fcX₂ (X = CH₂OH, COCl, CON₃, NCO, NHCOOMe, NHBoc, NH₂) were optimized and scaled up. The X-ray crystal structures of fc(COOEt)₂, fc(NCO)₂·¹/₂C₆H₆, and fc(NHCOOMe)₂·MeOH are reported.