2-chloro-6-fluoro-3-iodobenzonitrile

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-chloro-6-fluoro-3-iodobenzonitrile (800 mg, 2.85 mmol), allyltributylstannane (1.245 mg, 3.761 mmol), LiCl (431 mg, 10.3 mmol) and Pd(PPh3)4 (100 mg) in 50 mL toluene was heated at 100° C. overnight. Cooled to rt. and diluted with 50 mL EtOAc and filtered. The filtrate was washed with water and brine, dried over anhydrous Na2SO4 and concentrated to dryness. The residue was purified via prep-TLC (ethyl acetate/Pet ether=1:5) to give 2-chloro-6-fluoro-3-(prop-2-en-1-yl)benzonitrile. 1H-NMR (400 MHz, CDCl3) δ ppm 7.37˜7.41 (m, 1H), 7.01˜7.06 (m, 1H), 5.78˜5.87 (m, 1H), 4.99˜5.12 (m, 2H), 3.44 (d, J=6.3 Hz, 2H). Cooled to rt filtered The filtrate was washed with water and brine dried over anhydrous Na2SO4 concentrated to dryness The residue was purified via prep-TLC (ethyl acetate/Pet ether=1:5)