[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH3:23])=[CH:17][CH:16]=3)=[CH:11][C:10]=2[F:24])[CH:5]=[C:6]([F:8])[CH:7]=1.C([Li])CCC.CCCCCC.B(OC)(OC)[O:37]C.Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH3:23])=[CH:17][CH:16]=3)=[CH:11][C:10]=2[F:24])[CH:5]=[C:6]([F:8])[C:7]=1[OH:37]Under a nitrogen atmosphere, the 3,5-difluoro-[2-fluoro-4-(4-propylphenyl)phenyl]benzene (18.7 g) obtained in the process (1-1) was dissolved in THF (90 mL), and the solution was cooled to −40° C. or lower. Then, 1.6 mol/L of an n-butyllithium/hexane solution (40 mL) was added thereto at a rate which did not allow the internal temperature to be −35° C. or higher, and the product was stirred at −40° C. for an hour. Then, trimethyl borate (7.1 g) was added thereto at −40° C. at a rate which did not allow the internal temperature to be −35° C. or higher. The temperature was slowly increased to room temperature, the product was further stirred for 30 minutes at room temperature, 10% hydrochloric acid (50 mL) was subsequently added thereto under cooling with ice to separate the organic layer, and the organic layer was washed with a saturated salt solution. Then, a 30% hydrogen peroxide solution (8.4 g) was slowly added thereto, and then the product was stirred at 40° C. for 14 hours. The product was cooled with ice, and a 10% aqueous sodium sulfite solution was added thereto at a rate which did not allow the internal temperature to exceed 20° C., thereby separating the organic layer. Toluene was added to the water layer for extraction, the organic layer was added thereto and then washed with a saturated salt solution, and sodium sulfate was added thereto for dehydration. The solvent was distilled off under reduced pressure, and the product was purified by silica gel column chromatography and then recrystallized from hexane, thereby yielding 14.6 g of 2,6-difluoro-4-[2-fluoro-4-(4-propylphenyl)phenyl]phenol (A).
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