Hydrochloric Acid → 1-Iodo-3-methoxy-5-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-methoxy-5-nitro-phenylamine (7.5 g, 44.6 mmol) in water (20 mL) was added a concentrated hydrochloric acid (19.95 mL, 267.6 mmol, 36%) at 0° C. To this was added a chilled solution of sodium nitrite (5.62 g, 80.28 mmol) in water (28.4 mL) dropwise with a vigorous stirring. Then, the resulting colored mixture was stirred for 15 min at 0° C., and a cold solution of potassium iodide (14.81 g, 89.2 mmol) in water (28.4 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 (3×200 mL). The combined organic extracts were washed with brine solution (300 mL) and dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Then, the crude residue was purified by using a LC 120 column, eluting with 0-10% ethyl acetate in hexanes to obtain 1-iodo-3-methoxy-5-nitro-benzene (10 g, 80%) as a white solid: EI(+)-HRMS m/e calculated for C7H6INO3 (M+)+ 278.9392, found 278.9393.

Provenance & Evidence