36958-61-9

107-29-9

106-96-7

36958-61-9

To a stirred solution of acetaldoxime (10 g, 169.49 mmol) in dichloromethane (DCM, 200 mL) was added 3-bromopropargyl (13 mL, 169.49 mmol) followed by triethylamine (10 mL) at 0 °C. Then, 4% aqueous sodium hypochlorite solution (NaOCl, 1.08 mL) was added dropwise to the reaction mixture. The reaction mixture was stirred at 0 °C and then gradually warmed up to room temperature and continued stirring for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane (3 x 200 mL), the organic phases were combined and dried with anhydrous sodium sulfate (Na2SO4). The solvent was removed by concentration under reduced pressure to give the crude product. The crude product was purified by fast column chromatography (silica gel: 100-200 mesh), the eluent was 0-10% ethyl acetate (EtOAc) in hexane solution, and the final product was 5-(bromomethyl)-3-methylisoxazole (3 g, 11.2%) as a light yellow liquid. The structure of the product was confirmed by 1H-NMR (CDCl3, 400 MHz) with chemical shifts (ppm) of 6.18 (s, 1H), 4.42 (s, 2H), 2.31 (s, 3H).