[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH3:16])[CH2:12][CH:13]=2)=[C:4]([F:17])[CH:3]=1.C1(C)C=CC=CC=1>[Pd].CC(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH3:16])[CH2:10][CH2:9]2)=[C:4]([F:17])[CH:3]=1A mixture of compound (69) (39.2 g, 131.9 mmol) and 5%-palladium on carbon (0.5% sulfur, 50% water-containing article) (1.18 g, 3 wt %) was agitated for 18 hours under a hydrogen atmosphere in a toluene (200 mL)-IPA (100 mL) solvent. The reaction mixture was filtered and a solvent in a filtrate was distilled off by an evaporator. The residue was passed through silica gel column chromatography and then a low-boiling-point material was distilled off by distillation, and thus 4-bromo-2-fluoro-1-(4-propylcyclohexyl)benzene (70) (30.8 g, yield 78.1%) was obtained.
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