Iodine → 2-(3-Fluoro-4-iodophenyl)naphthalene

Participants

Reaction Steps

A 50.21 ml cyclohexane solution of sec-butyl lithium in a concentration of 1.01M was dropped into a 200 ml THF solution of 4.90 g (=22.05 mmol) of the above 2-(3-fluorophenyl)naphthalene at −70° C. After the dropping was finished, the reaction solution was stirred at the same temperature for 1 hour, added with a 200 ml THF solution of 12.87 g (=50.71 mmol) of iodine through dropping and then slowly heated to room temperature. After being stirred for 18 hours, the reaction solution was added into iced water dissolved with Na2S2O3.5H2O, and then the reaction mixture was extracted twice with toluene. The extract was washed thrice with water and then dried with anhydrous MgSO4. After the solvent was evaporated under a reduced pressure, the obtained orange solid of 8.61 g was purified with silica gel chromatography using heptane/toluene in a ratio of 5:1 as the eluent to obtain a pinkish solid of 7.86 g, which was recrystallized with a mixed solvent of Solumix/heptane/toluene in a ratio of 5:5:1 to obtain 6.00 g of 2-(3-fluoro-4-iodophenyl)naphthalene as yellowish crystals.

Provenance & Evidence