Abstract: Bromination of ten known fluorinated quinolin-2(1H)-ones by the KBrO3/HBr system is investigated. If there is no F atom in the position 6 of substrate, the Br atom is introduced into position 3 or 6 to form monobromo derivative, the second Br atom is introduced into the same positions leading to 3,6-dibromo product. If a F atom is in position 6, the 3-bromo product is initially obtained, which gives a 3,5-dibromo or 3,8-dibromo derivatives upon further bromination depending on the F atoms positions. In this case, when both positions 5 and 8 of 3- bromoquinolin-2(1H)-one are unsubstituted, the second Br atom is introduced into position 8. If there are more than two F atoms in the benzene moiety, the sole 3-bromo product is obtained. Relative (ΔE) energies of the considered σ− complexes estimated by DFT calculations for the reactions in question are consistent with the experimentally observed regioselectivity.

Cite: Verkhov F.K. , Skolyapova A.D. , Krasnov V.I. , Bagryanskaya I.Y. , Andreev R.V. , Karpova E.V. , Kalizhnikova E.E. , Selivanova G.A.
Bromination of quinolin-2(1H)-ones fluorinated on the benzene moiety
Journal of Fluorine Chemistry. 2023. V.268. P.110132. DOI: 10.1016/j.jfluchem.2023.110132 WOS РИНЦ

Dates:

Published online:	Apr 21, 2021
Submitted:	Apr 5, 2023
Accepted:	Apr 14, 2023
Published print:	Apr 14, 2023

Identifiers:

Web of science	WOS:000983006300001
Elibrary	64628441
OpenAlex	W4366608227

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