98519-65-4

yellow powder

4-Bromo-7-chloroquinoline is a chemical reagent in the synthesis of autophagy antitumor inhibitors, as well as antifungal agents.

The Journal of Organic Chemistry, 72, p. 2232, 2007 DOI: 10.1021/jo062168u

General procedure for the synthesis of 4-bromo-7-chloroquinoline from 4,7-dichloroquinoline: 4,7-dichloroquinoline (0.3315 g, 1.674 mmol) and propionitrile (3 mL) were added in a 20 mL microwave tube, followed by the slow addition of trimethylsilyl bromide (TMS-Br, 0.434 mL, 3.35 mmol) at room temperature. Precipitation generation was observed during the reaction. The reaction tube was sealed and placed in a 100 °C oil bath for 12 hours. After completion of the reaction, the system was cooled to room temperature. The crude reaction mixture was slowly poured into pre-cooled sodium hydroxide solution (1 N, 3 mL) and the reaction tube was rinsed with an appropriate amount of water. Subsequently, the aqueous layer was extracted with ether (3 x 5 mL). All ether layers were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to afford the target product 4-bromo-7-chloroquinoline (300 mg, 1.126 mmol, 67% yield) as a yellow solid. The product was confirmed by NMR hydrogen spectrum (400 MHz, CDCl3): δ 8.70 (d, J = 4.6 Hz, 1H), 8.17 (d, J = 8.8 Hz, 1H), 8.14 (d, J = 2.0 Hz, 1H), 7.73 (d, J = 4.6 Hz, 1H), 7.63 (dd, J = 9.0, 2.0 Hz, 1H); liquid chromatography-mass spectrometry (LCMS, ESI) showed a molecular ion peak m/z of 241.9, which is consistent with the calculated value of C9H5BrClN.

[1] European Journal of Organic Chemistry, 2002, # 24, p. 4181 - 4184
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[3] Patent: WO2017/59085, 2017, A1. Location in patent: Page/Page column 224; 225