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

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.

1. temperatureThen, the resulting light yellow suspension was heated
2. temperatureto reflux for 48 h
3. extractionThe organic compound was extracted into ethyl acetate (2×75 mL)
4. washthe combined ethyl acetate extracts were washed with saturated sodium thiosulfate solution (100 mL)
5. customto remove the iodine color
6. washwas also washed with brine solution (100 mL)
7. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe crude residue was purified
11. washeluting with 0-20% ethyl acetate in hexanes

ORD record

ord-56b5ad04b8d54af4899e9d5889ca765d

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08093385B2