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1239460-75-3

Concentrated sulfuric acid (2.2 mL) was added dropwise to a mixture of 5-bromo-2-(trifluoromethyl)aniline (3.0 g, 12.6 mmol), glycerol (4.64 g, 50.0 mmol) and ferrous sulfate (0.56 g, 2.0 mmol). The reaction mixture was heated and stirred at 120 °C for 4 hours. After completion of the reaction, it was cooled to room temperature, the reaction mixture was diluted with ethyl acetate (150 mL) and the pH was adjusted with 2N aqueous sodium hydroxide to about 13. The organic layer was separated, washed with saturated brine, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by fast column chromatography to afford 5-bromo-8-(trifluoromethyl)quinoline (1.2 g, 48% yield).