N-Iodosuccinimide → 5-(2-hydroxyethyl)-6-iodo-2-benzofuran-1(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of 5-(2-hydroxyethyl)-2-benzofuran-1(3H)-one (9.00 g, 50.6 mmol) in 100 mL of TfOH was added NIS (12.5 g, 55.6 mmol), then the mixture was stirred at 0° C. for 2 hrs and then poured into ice-water (500 mL). The solution was extracted with EtOAc (3×500 mL) and the combined organic layers were washed with saturated NaHCO3 solution and brine, and dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica column chromatography (EtOAc/Petrol Ether=1:5) to give 5-(2-hydroxyethyl)-6-iodo-2-benzofuran-1(3H)-one and its separated regioisomer.

Provenance & Evidence