[CH2:1]([O:3][C:4]1[C:5]([F:21])=[C:6]([CH:19]=[O:20])[C:7]([C:10]2[C:11]([CH:17]=[O:18])=[C:12]([F:16])[CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1)[CH3:2].C(N(CC)CC)C>[Br-].C([N+]1C(C)=C(CCO)SC=1)C.CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]2[C:10]3[C:11](=[C:12]([F:16])[CH:13]=[CH:14][CH:15]=3)[C:17](=[O:18])[C:19](=[O:20])[C:6]=2[C:5]=1[F:21])[CH3:2]Under a nitrogen atmosphere, a DMF (50 mL) solution of compound (85) (10.0 g, 3.45 mmol), 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazole-3-iumbromide (1.74 g, 6.89 mmol) and triethylamine (1.05 g, 10.34 mmol) was agitated at 60° C. for 6 hours. The reaction mixture was quenched with 150 mL of water, and extracted with 50 mL of dichloromethane three times. Combined organic layers were washed with a 1N hydrochloric acid aqueous solution, water and saturated brine, and then dried over magnesium sulfate, and a solvent was distilled off by an evaporator. The residue was washed with toluene, and thus 2-ethoxy-1,8-difluorophenanthrene-9,10-dione (86) (7.0 g, yield 70.5%) was obtained.
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