General procedure for the synthesis of 1,3-difluoro-5-iodobenzene from 3,5-difluorophenylboronic acid: 0.05 mmol of Cu(NO3)2-3H2O, 1 mmol of I2, 1 mmol of 3,5-difluorophenylboronic acid, and 0.8 mL of acetonitrile were added to a 15 mL reaction tube. The reaction tube was sealed and the reaction was carried out under no inert gas protection for 6 hours. Upon completion of the reaction, the reaction was terminated by adding 10 mL of water. The mixture was extracted with dichloromethane (3 x 15 mL). The organic layers were combined, washed sequentially with aqueous sodium thiosulfate and distilled water, dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purified by column chromatography and structurally characterized by 1H NMR, 13C NMR or GC-MS.
