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 TammEfficient and simple methods for
the large-scale preparation of
1,1′-ferrocenedicarboxylic acid, fc(COOH)<sub>2</sub>, involving
the sodium salts of cyclopentadienecarboxylic methyl and ethyl esters,
Na(C<sub>5</sub>H<sub>4</sub>COOR) (R = Me, Et), are presented. With
fc(COOH)<sub>2</sub> at hand, the syntheses of various 1,1′-disubstituted
compounds of the type fcX<sub>2</sub> (X = CH<sub>2</sub>OH, COCl,
CON<sub>3</sub>, NCO, NHCOOMe,
NHBoc, NH<sub>2</sub>) were optimized and scaled up. The X-ray crystal
structures of fc(COOEt)<sub>2</sub>, fc(NCO)<sub>2</sub>·<sup>1</sup>/<sub>2</sub>C<sub>6</sub>H<sub>6</sub>, and fc(NHCOOMe)<sub>2</sub>·MeOH are reported.
