At room temperature, a solution of tert-butyl nitrite (7.5 mL, 63.5 mmol, 225 μM) and iodine (381 mg, 1.5 mmol) in anhydrous acetonitrile (10 mL) was added to a solution of 3-aminobenzonitrile (177 mg, 1.5 mmol) in anhydrous acetonitrile (10). The mixture was heated at 60°C for 25 minutes, and a saturated aqueous solution of sodium thiosulfate (20 mL) was added. The mixture was concentrated under reduced pressure to remove most of the acetonitrile, and the aqueous phase was extracted with EtOAc (4 × 10 mL). The combined organic matter was dried over MgSO4. The mixture was filtered and concentrated under reduced pressure to give a solid. The solid was pre-added to silica.
The residue was purified by rapid column chromatography, eluting with a heptane solution of 40 g silica and 0-10% EtOAc. The fractions carrying the product were combined and evaporated to obtain the product, 3-Iodobenzonitrile.
