179055-20-0

916766-83-1

(C) Synthesis of 3-(4-(chloromethyl)phenyl)-1-methyl-1H-pyrazole: [4-(1-methyl-1H-pyrazol-3-yl)phenyl]methanol (1.00 g) was dissolved in THF (15.0 mL), and thionyl chloride (0.58 mL) was added slowly and dropwise under cooling in an ice bath. The reaction mixture was stirred at 17 °C for 16 hours. After the reaction was completed, it was diluted with water and ethyl acetate and neutralized by adding saturated aqueous sodium bicarbonate. The organic layer was separated, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane) to afford the target product 3-(4-(chloromethyl)phenyl)-1-methyl-1H-pyrazole (0.65 g). NMR (300 MHz, CDCl3) δ 3.95 (3H, s), 4.61 (2H, s), 6.49-6.57 (1H, m). 7.33-7.44 (3H, m), 7.74-7.82 (2H, m).