2-Fluoro-4-iodoaniline → 4-Amino-3-fluorobenzonitrile

Participants

Reaction Steps

A 50 ml of two-neck round bottom flask was filled with argon gas, and the solution of 2-fluoro-4-iodoaniline (1 g, 5.219 mmol, 1 equiv.) in DMF was put into the flask. To the solution was added Copper (I) cyanide (453.4 mg, 5.063 mmol, 1.2 equiv.) and heated to reflux for 5 hours. After confirming the completion of the reaction with TLC, saturated sodium bicarbonate solution was added to the solution and stirred for 5 minutes. The resulting solution was extracted with methylenechloride, washed with water and brine, dried over Na2SO4, filtered and evaporated. The obtained liquid was column-chromatographed (n-hexane/ethyl acetate=2/1) to yield a pale yellow solid (461.6 mg).

Provenance & Evidence