Sodium Iodide → 3-Iodo-5-thiophen-3-yl-phenol

Participants

Reaction Steps

To a suspension of 3-(3-iodo-5-methoxy-phenyl)-thiophene (2.08 g, 6.7 mmol) and sodium iodide (65.73 mmol, 9.85 g) in acetonitrile (80 mL) was added trimethylsilyl chloride (32.86 mmol, 4.16 mL) at room temperature. Then, the resulting light yellow suspension was heated to reflux for 48 h. Then, it was cooled to room temperature and diluted with water (50 mL). The organic compound was extracted into ethyl acetate (2×75 mL) and the combined ethyl acetate extracts were washed with saturated sodium thiosulfate solution (100 mL) to remove the iodine color and was also washed with brine solution (100 mL). Then, the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by using an ISCO 120 g column, eluting with 0-20% ethyl acetate in hexanes to obtain 3-iodo-5-thiophen-3-yl-phenol (1.92 g, 97%) as a light brown oil: ES(+)-HRMS m/e calculated for C10H7IOS (M−H)+ 300.9189, found 300.9189.

Provenance & Evidence