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Dimethyl 4,5-di­chloro­phthalate

While endeavoring to synthesize new chlorinated ligands for ruthenium-based metathesis catalysts, the title compound dimethyl 4,5-di­chloro­phthalate, C(10)H(8)Cl(2)O(4), was prepared from commercially available 4,5-di­chloro­phthalic acid in ∼77% yield. The title mol­ecule, which also finds utility...

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Detalles Bibliográficos
Autores principales: Hickstein, Daniel D., Reinheimer, Eric W., Johnson, Adam R., O’Leary, Daniel J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9462297/
https://www.ncbi.nlm.nih.gov/pubmed/36340982
http://dx.doi.org/10.1107/S2414314621010439
Descripción
Sumario:While endeavoring to synthesize new chlorinated ligands for ruthenium-based metathesis catalysts, the title compound dimethyl 4,5-di­chloro­phthalate, C(10)H(8)Cl(2)O(4), was prepared from commercially available 4,5-di­chloro­phthalic acid in ∼77% yield. The title mol­ecule, which also finds utility as a precursor mol­ecule 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 inter­actions 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 mol­ecules parallel to b. [Image: see text]