Iodine chloride → 6-Amino-2-fluoro-3-iodobenzonitrile

Participants

Reaction Steps

To a solution of 2-amino-6-fluorobenzonitrile (3 g, 0.022 mol) in CH2Cl2 (200 mL) and MeOH (50 mL) was added sodium bicarbonate (3.7 g, 0.044 mmol) and ICl (3.75 g, 0.023 mol) in CH2Cl2 (20 mL). The suspension was stirred at room temperature for 2 h. The reaction mixture was concentrated and the residue was partitioned between CH2Cl2 and water. The organic layer was washed with Na2S2O3, water, and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude material was triturated with ether. Filtration gave the title compound as a brown solid (2.5 g, 43% yield). LC/MS: Example 104A @ 2.86 min (RT) (Condition G). MS (ES): m/z=262.93, [M+H]+. 1H NMR (400 MHz, CDCl3) δ ppm 7.60 (1 hr, dd, J=8.78, 7.03 Hz), 6.39 (1 hr, d, J=8 Hz).

Provenance & Evidence