288-32-4

5467-74-3

10040-96-7

A magnetic stirrer, imidazole (59 mg, 0.5 mmol), 4-bromophenylboronic acid (1.0 mmol), cuprous sulfide (4 mg, 0.025 mmol), and methanol (2 mL) were added to a 10 mL round bottom flask followed by N,N,N',N'-tetramethylethylenediamine (TMEDA, 0.075 mL, 0.5 mmol). The flask was sealed with a rubber septum and an 18-gauge needle was inserted to allow air to enter the reaction system while preventing contamination of the mixture. The reaction mixture was stirred at 400 to 600 rpm for an appropriate time. After completion of the reaction, the reaction mixture was extracted with ethyl acetate (2 x 15 mL). The organic layers were combined and washed with saturated aqueous ethylenediaminetetraacetic acid disodium salt solution (15 mL), followed by drying with anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to afford the target product 1-(4-bromophenyl)imidazole. The structure of the product was characterized by 1H NMR, 13C NMR, high resolution mass spectrometry (HRMS) and melting point (if solid).