2301-25-9

288-32-4

24067-17-2

2301-25-9

A magnetic stirrer, imidazole (59 mg, 0.5 mmol), 4-nitrophenylboronic acid (1.0 mmol), cuprous sulfide (4 mg, 0.025 mmol), and methanol (2 mL) were sequentially 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 through the septum to ensure that the reaction system was in contact with air while avoiding external contamination. The reaction mixture was placed on a magnetic stirrer and 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 phases were combined and washed with saturated aqueous ethylenediaminetetraacetic acid disodium salt solution (15 mL) and subsequently dried over 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 gradient) to afford the target product 1-(4-nitrophenyl)-1H-imidazole. The structure of the product was confirmed by 1H NMR, 13C NMR, high resolution mass spectrometry (HRMS) and melting point (if solid).