To a solution of 5-iodo-1(H)-imidazole (3.5 g, 18.0 mmol) in DMF (70 mL) was added triethylamine (TEA, 3.0 mL, 21.7 mmol) and triphenylmethane chloride (5.5 g, 19.7 mmol). The reaction mixture was stirred at 20°C for 24 hours. Upon completion of the reaction, the solution was poured into water to quench the reaction. The precipitated solid was collected by filtration to give the crude product. The crude product was purified by rapid column chromatography on silica gel to afford 1-trityl-4-iodoimidazole (4) as a white solid (7.4 g, 94.0% yield). Melting point: 148-150 °C. 1H NMR (300 MHz, chloroform-d) δ (ppm): 6.9 (m, 1H), 7.0-7.2 (m, 6H), 7.25-7.4 (m, 10H). Mass spectrum (EI) m/z: 437.1 [MH]+.
