Hydrochloric Acid → 3-Iodo-1-methanesulfonyl-5-methoxy-benzene

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-methanesulfonyl-5-methoxy-phenylamine (1.0 g, 4.94 mmol) in water (2.66 mL) was added a concentrated hydrochloric acid (2.21 mL, 29.66 mmol, 36%) at 0° C. To this mixture was added a chilled solution of sodium nitrite (0.622 g, 8.89 mmol) in water (3.78 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 (1.64 g, 9.88 mmol) in water (3.78 mL) was added carefully. During this addition, a black brown solid was formed and after addition the ice bath was removed, and the reaction mixture was stirred for 2 days at room temperature. Then, the reaction mixture was diluted with water (50 mL) and saturated sodium thiosulfate solution (100 mL). The organic compound was extracted into ethyl acetate (3×50 mL). The combined organic extracts were washed with brine solution (100 mL) and dried over anhydrous magnesium sulfate. The filtration of the drying agent and concentration of the filtrate under reduced pressure gave the crude residue which was purified by using a silica gel column, eluting with 0-35% ethyl acetate in hexanes to obtain 3-iodo-1-methanesulfonyl-5-methoxy-benzene (1.08 g, 70%) as a white solid: ES(+)-HRMS m/e calcd for C8H9IO3S (M+H)+ 312.9390, found 312.9390.

Provenance & Evidence