Cl[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=[O:5].[CH2:11]([O:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[C:16]([CH:23]=[O:24])[C:15]=1[F:25])[CH3:12].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].O.C(O)C>[CH2:11]([O:13][C:14]1[C:15]([F:25])=[C:16]([CH:23]=[O:24])[C:17]([C:2]2[C:3]([CH:4]=[O:5])=[C:6]([F:10])[CH:7]=[CH:8][CH:9]=2)=[CH:18][CH:19]=1)[CH3:12]Under a nitrogen atmosphere, a mixture of 2-chloro-6-fluorobenzaldehyde (84) (50.0 g, 315 mmol), compound (55) (73.5 g, 347 mmol), Pd-132 (made by Johnson Matthey Catalysis and Chiral Technologies) (0.223 g, 0.315 mmol), potassium carbonate (87 g, 631 mmol) and TBAB (20.33 g, 63.1 mmol) was refluxed in a toluene 500 mL)-ethanol (100 mL)-water (500 mL) solvent for 5 hours. The reaction mixture was extracted with 300 mL of toluene three times. Combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, and then dried over magnesium sulfate, and a solvent was distilled off by an evaporator. The residue was purified by silica gel column chromatography, and thus 4-ethoxy-3,3′-difluoro-[1,1′-biphenyl]-2,2′-dicarboaldehyde (85) (77.25 g, yield 84%) was obtained.
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