Example 17: Preparation of 3-(bromomethyl)-2-cyclopropyl-4-(4-fluorophenyl)quinoline (PTVBR)
PTVME (0.85 g, 3.06 mmol) and N-bromosuccinimide (NBS, 1.16 g, 2.1 eq.) were dissolved in a solvent mixture of acetonitrile (MeCN, 20 mL) and carbon tetrachloride (CCl4, 5 mL). The reaction mixture was irradiated for 4 days at room temperature (~20 °C) using light at a wavelength of 254 nm. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the residual oil was redissolved in dichloromethane (CH2Cl2, 20 mL). The organic phase was washed sequentially with saturated sodium thiosulfate solution (Na2S2O3, 1 × 10 mL), saturated sodium bicarbonate solution (NaHCO3, 2 × 10 mL), and brine (1 × 10 mL) and dried with anhydrous magnesium sulfate (MgSO4). After removing the solvent under reduced pressure, the product was purified by column chromatography (elution gradient: 1-10% ethyl acetate/n-heptane solution) to give PTVBR (0.22 g, 20% yield).
1H NMR (CDCl3): δ 1.17 (2H, m), 1.40 (2H, m), 2.50-2.54 (1H, m), 4.6 (2H, s), 7.24-7.40 (6H, m), 7.64 (1H, m), 8.00-8.02 (1H, m) ppm.
13C NMR (CDCl3): δ 9.8, 14.7, 29.1, 115.6, 115.8, 125.8, 126.2, 126.4, 127.4, 128.5, 128.8, 129.7, 130.87, 130.91, 131.0, 131.60, 131.63, 146.9, 147.1. 161.4, 161.5, 163.9 ppm.
