A mixture of 7.00 g (=18.61 mmol) of the above 2-[2-(3-fluoro-4-iodophenyl)ethyl]naphthalene, 3.12 g (=22.30 mmol) of 4-fluorophenylboric acid, 3.86 g (=27.93 mmol) of K2CO3, 1.50 g (=4.65 mmol) of tetrabutylammonium bromide, 0.39 g (=0.56 mmol) of dichlorobis(triphenylphosphine)palladium(II), 0.30 g (1.12 mmol) of triphenylphosphine and 60 ml of a mixed solvent of toluene/water/ethanol in a ratio of 1:1:1 was stirred for 4 hours with reflux. The reaction mixture obtained was extracted thrice with toluene, and then the extract was washed thrice with water and dried with anhydrous MgSO4. After the solvent was evaporated under a reduced pressure, the obtained orange solid of 8.48 g was purified with silica gel chromatography using heptane/toluene in a ratio of 5:1 as the eluent to obtain a white solid of 7.37 g, which was further recrystallized using a mixed solvent of Solumix/heptane in a ratio of 1:1 to obtain the target compound in an amount of 5.02 g. The product was characterized as the target compound based on results of various instrumental analyses, and the phase transition of the product is notated as “C 108.1 I”.
