3-FLUORO-4-IODOBENZONITRILE

63069-50-1

887266-99-1

The general procedure for the synthesis of 3-fluoro-4-iodobenzonitrile from 3-fluoro-4-aminobenzonitrile was as follows: a mixture of 4-amino-3-fluorobenzonitrile (5.0 g, 36.76 mmol) with 4-toluenesulfonic acid (20.0 g, 105.2 mmol) in acetonitrile (50 mL) was stirred for 4 hours at room temperature. Subsequently, an aqueous solution of NaNO2 (3.8 g, 55.07 mmol) and KI (9.15 g, 55.07 mmol) was slowly added at 0 °C and stirring was continued for 1 hour. After completion of the reaction, the reaction mixture was quenched with ice water, washed sequentially with aqueous NaHSO3 and extracted with EtOAc. The organic layer was washed with water and brine, dried with Na2SO4 and concentrated under reduced pressure to give 4.0 g of the target product 3-fluoro-4-iodobenzonitrile. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 7.94-7.89 (t, J = 8.4 Hz, 1H), 7.34-7.32 (d, J = 7.5 Hz, 1H), 7.21-7.19 (d, J = 8.1 Hz, 1H).