[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([OH:11])[CH:7]=[CH:8][C:9]=1[F:10].[F:12][C:13]1[CH:18]=[C:17]([CH2:19][CH2:20][CH3:21])[CH:16]=[CH:15][C:14]=1[C:22]1[CH:27]=[CH:26][C:25]([CH2:28]Br)=[C:24]([F:30])[CH:23]=1.Cl>CN(C)C=O>[F:3][C:4]1[CH:5]=[C:6]([O:11][CH2:28][C:25]2[CH:26]=[CH:27][C:22]([C:14]3[CH:15]=[CH:16][C:17]([CH2:19][CH2:20][CH3:21])=[CH:18][C:13]=3[F:12])=[CH:23][C:24]=2[F:30])[CH:7]=[CH:8][C:9]=1[F:10]Into the mixture of 0.6 g (13.8 mmol) of NaH and 3 ml of dimethyl formamide (DMF), a solution of 1.8 g (13.8 mmol) of 3,4-difluorophenol dissolved in 20 ml of DMF was added dropwise, and the mixture was stirred for 1 hour. Into this mixture, 3.0 g (9.2 mmol) of 2′-fluoro-4′-propyl-3-fluoro-4-bromomethylbiphenyl was added, and the mixture was heated and refluxed for 4 hours. The reaction mixture was poured into 50 ml of 1N-HCl and extracted by 100 ml of ethyl acetate, and the obtained organic layer was washed twice with a diluted NaHCO3 solution and three times with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was subjected to a silica gel column chromatograph (eluent: heptane) to obtain crude (2′-fluoro-4′-propyl-3-fluorobiphenyl-4-yl)methyl 3,4-difluorophenyl ether.
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