Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3C4C([C:18]5[C:23]=3[C:22]=2[CH:21]=[CH:20][CH:19]=5)=CC=CC=4)=[CH:4][CH:3]=1.C([Li])CCC.[B:29](OC(C)C)([O:34]C(C)C)[O:30]C(C)C.Cl.[CH3:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]>O1CCCC1>[CH:20]1[C:21]2=[C:22]3[C:8]([C:5]4[C:6]2=[CH:7][CH:2]=[CH:3][CH:4]=4)=[CH:9][CH:10]=[CH:11][C:23]3=[C:18]([C:45]2[CH:44]=[CH:43][C:48]([B:29]([OH:34])[OH:30])=[CH:47][CH:46]=2)[CH:19]=1
In the atmosphere of argon, 9.2 g of 3-(4-bromophenyl)fluoranthene and 129 mL of tetrahydrofuran were placed in a flask. The reaction solution was cooled to −70° C., and 17.2 mL of a 1.65M hexane solution of n-butyllithium was added dropwise. Stirring was conducted at −70° C. for 2 hours. To the reaction solution, 17.7 mL of triisopropyl borate was added dropwise, and the resultant was stirred at −70° C. for 1 hour. While heating the reaction solution to room temperature, stirring was conducted for 5 hours. 2M hydrochloric acid was added to the reaction liquid to allow it to be acidic, and the reaction solution was extracted with ethyl acetate. After removing an aqueous phase, an organic phase was washed with saturated saline, and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, residues were washed with a hexane-ethyl acetate mixed solution, whereby 7.9 g (yield 95%) of 4-(fluoranthen-3-yl)phenylboronic acid was obtained.
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