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The synthesis of new 6-Bromoquinolin-4-ol derivatives (<b>3a</b>–<b>3h</b>) by Chan–Lam coupling utilizing different types of solvents (protic, aprotic, and mixed solvents) and bases was studied in the present manuscript. Furthermore, their potential against ESBL producing <i>Escherichia coli</i> (ESBL <i>E. coli</i>) and methicillin-resistant <i>Staphylococcus</i><i>aureus</i> (MRSA) were investigated. Commercially available 6-bromoquinolin-4-ol (<b>3a</b>) was reacted with different types of aryl boronic acids along with Cu(OAc)₂ via Chan–Lam coupling methodology utilizing the protic and aprotic and mixed solvents. The molecules (<b>3a</b>–<b>3h</b>) exhibited very good yields with methanol, moderate yields with DMF, and low yields with ethanol solvents, while the mixed solvent CH₃OH/H₂O (8:1) gave more excellent results as compared to the other solvents. The in vitro antiseptic values against ESBL <i>E. coli</i> and MRSA were calculated at five different deliberations (<b>10</b>, <b>20</b>, <b>30</b>, <b>40</b>, <b>50</b> mg/well) by agar well diffusion method. The molecule <b>3e</b> depicted highest antibacterial activity while compounds <b>3b</b> and <b>3d</b> showed low antibacterial activity. Additionally, MIC and MBC standards were calculated against the established bacteria by broth dilution method. Furthermore, a molecular docking investigation of the derivatives (<b>3a</b>–<b>3h</b>) were performed. Compound (<b>3e</b>) was highly active and depicted the least binding energy of −5.4. Moreover, to investigate the essential structural and physical properties, the density functional theory (DFT) findings of the synthesized molecules were accomplished by using the basic set PBE0-D3BJ/def2-TZVP/SMD water level of the theory. The synthesized compounds showed an energy gap from 4.93 to 5.07 eV.