Dimethyl 4,5-di-chloro-phthalate

IUCrdata. 2021 Oct 13;6(Pt 10):x211043. doi: 10.1107/S2414314621010439. eCollection 2021 Oct.


While endeavoring to synthesize new chlorinated ligands for ruthenium-based metathesis catalysts, the title compound dimethyl 4,5-di-chloro-phthalate, C10H8Cl2O4, was prepared from commercially available 4,5-di-chloro-phthalic acid in ∼77% yield. The title mol-ecule, which also finds utility as a precursor mol-ecule for the synthesis of drugs used in the treatment of Alzheimer’s disease, shows one carbonyl-containing methyl ester moiety lying nearly co-planar with the chlorine-derivatized aromatic ring while the second methyl ester shows a significant deviation of 101.05 (12)° from the least-squares plane of the aromatic ring. Within the crystal, structural integrity is maintained by the concerted effects of electrostatic inter-actions involving the electron-deficient carbonyl carbon atom and the electron-rich aromatic ring along the a-axis direction and C-H⋯O hydrogen bonds between neighboring mol-ecules parallel to b.

PMID:36340982 | PMC:PMC9462297 | DOI:10.1107/S2414314621010439


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