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Step 1: Synthesis of 5-bromo-8-methylquinoline 8-Methylquinoline (0.3 M) was dissolved in concentrated H2SO4, Ag2SO4 (1.5 equiv) and bromine (1.0 equiv) were added. The reaction mixture was stirred at room temperature for 5 hours and then poured into ice water to quench the reaction. The precipitate was removed by filtration and the filtrate was alkalized with saturated aqueous Na2CO3 to pH > 7. The aqueous phase was extracted with EtOAc (3×), the organic layers were combined and dried over anhydrous Na2SO4. The organic phase was concentrated under reduced pressure to afford the target product 5-bromo-8-methylquinoline in 71% yield as a white solid. Mass spectrum (ESI+) m/z: 222, 224 [M+H]+.

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