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

Participants

Reaction Steps

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.

Provenance & Evidence