Hydrochloric Acid → 3-(3-Iodo-5-methoxy-phenyl)-thiophene

To a solution of 3-methoxy-5-thiophen-3-yl-phenylamine (2.45 g, 11.93 mmol) in water (7.2 mL) was added a concentrated hydrochloric acid (5.34 mL, 71.58 mmol, 36%) at 0° C. To this was added in a dropwise manner to a vigorously stirred, chilled solution of sodium nitrite (1.5 g, 21.47 mmol) in water (9.3 mL). Then, the resulting colored mixture was stirred for 15 min at 0° C., and a cold solution of potassium iodide (3.96 g, 23.86 mmol) in water (9.3 mL) was added carefully. During this addition, a black brown solid was formed and after addition the ice-cold bath was removed, and the reaction mixture was heated to reflux. When the production of purple vapor ceased, the mixture was cooled to room temperature and the organic compound was extracted into dichloromethane (3×100 mL). The combined organic extracts were washed with brine solution (200 mL) and dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Then, the crude residue was purified by using a LC 80 column, eluting with 0-10% ethyl acetate in hexanes to obtain 3-(3-iodo-5-methoxy-phenyl)-thiophene (2.19 g, 58%) as a white solid: ES(+)-HRMS m/e calculated for C11H9IOS (M+)+ 315.9419, found 315.9418.

1. additionTo this was added in a dropwise manner to
2. stirringThen, the resulting colored mixture was stirred for 15 min at 0° C.
3. additionDuring this addition
4. customa black brown solid was formed
5. customwas removed
6. temperaturethe reaction mixture was heated to reflux
7. extractionthe organic compound was extracted into dichloromethane (3×100 mL)
8. washThe combined organic extracts were washed with brine solution (200 mL)
9. dry with materialdried over anhydrous magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThen, the crude residue was purified
13. washeluting with 0-10% ethyl acetate in hexanes

ORD record

ord-4cc566de00df401b8184bb25033ec6b6

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08093385B2