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Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C-F…H-C bond

Article scientifique 2019 Anglais

Résumé

4-(2-fluorophenyl)-7-methoxycoumarin (6) was synthesized by Pechmann reaction under mild conditions via a three step-reaction. The solution-state 1H NMR spectra of 6 showed a strong intramolecular interaction between F and H5 (J FH = 2.6 Hz) and 13C NMR suggested that this C-F…H-C coupling is a through-space interaction. The 2‑D HOESY spectrum and 1H‑{19F} 1‑D spectrum were also done to confirm this F…H interaction. The single crystal X-ray structure and the DFT-optimized structure showed that the fluorinated phenyl ring favours the orientation with the fluorine atom is closer to H5 than H3. The X-ray structure also showed the existence of the intermolecular C-F…H-C interactions.

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Mzozoyana, V., Heerden, F., Grimmer, C. (2019). Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C-F…H-C bond. https://doi.org/10.3762/bxiv.2019.124.v1

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Auteur(s)

Vuyisa Mzozoyana Fanie R. van Heerden Craig D. Grimmer

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