Br[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[F:9].[F:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][C:12]=1[CH:20]=[O:21].C([O-])([O-])=O.[Na+].[Na+].O>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=1[C:14]1[CH:15]=[CH:16][C:11]([F:10])=[C:12]([CH:20]=[O:21])[CH:13]=1To a solution of 2-bromo-1,3-difluorobenzene (100 g, 477.46 mmol) and 4-fluoro-3-formylphenylboronic acid (96.2 g, 572.95 mmol) in toluene (1432 mL) at RT was added Na2CO3 (2M in H2O) (477.46 mL, 954.2 mmol) and PdCl2(dppf) (7.798 g, 9.54 mmol). The reaction mixture was stirred at 100° C. for 8 h and cooled to RT. Water was added to the reaction mixture and extracted with EtOAc (2×500 mL). Organic layer was washed with brine and dried over Na2SO4. The organic layer was concentrated and purified by column using silica (100-200 mesh) and 0-5% EtOAc-hexane to provide 2′,4,6′-trifluorobiphenyl-3-carbaldehyde (54.3 g, 49.4% yield).
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