274-09-9

5876-51-7

N-iodosuccinimide (14.8 g, 66.0 mmol), 1,3-benzodioxole (6.31 mL, 55.0 mmol) and acetic acid (470 mL) were added to a 1 L flask under argon protection. The reaction mixture was stirred at room temperature for 65 hours. Upon completion of the reaction, the acetic acid was removed by distillation under reduced pressure and the residue was neutralized with saturated aqueous sodium bicarbonate solution. Subsequently, aqueous sodium thiosulfate and chloroform were added to the reaction mixture to separate the organic layer. The aqueous layer was further extracted with chloroform. All organic layers were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using hexane as eluent to afford 5-iodo-1,3-benzodioxole (11.3 g, 45.7 mmol, 83% yield) in colorless liquid form.