8-bromo-6-tert-butylquinoline

Preparation

2-Bromo-4-tert-butylaniline (7.41 g, 32.5 mmol), phloroglucinol (1.07 g, 8.5 mmol) and hydrochloric acid (37%, 0.5 mL) were added in a 100 mL flask. The flask was heated in an oil bath at 120℃ for 4 hours. After cooling down to room temperature, ethanol (20 mL) was added to the flask and the solid was crashed. The suspension was filter off and the solid was further washed with ethanol (40 mL) to give 8-bromo-6-tert-butylquinoline as colourless powder (5.46 g, 7.2 mmol, 85%). m.p. 230℃.
1H NMR (600 MHz, DMSO-d6) δ (ppm) = 7.50 (d, J = 2.2 Hz, 3H), 7.30 (dd, J = 8.5, 2.2 Hz, 3H), 7.26 (d, J = 8.5 Hz, 3H), 7.22 (s, 3H), 6.12 (s, 3H), 1.24 (s, 27H). 13C NMR (150 MHz, DMSO-d6) δ (ppm) =145.53, 145.35, 138.67, 129.53, 125.09, 121.56, 115.34, 97.60, 33.96, 31.03. IR (KBr) ? (cm-1 ) = 3397, 2962, 2903, 2867, 1597, 1512, 1491, 1389, 1362, 1307, 1266, 1176, 1117, 1041, 876, 855, 816, 731, 690, 599, 421. HRMS (ESI) (m/z): [M+H] + calculated. for C36H43N3Br3, 754.1007; found, 754.1005