[F:1][CH:2]1[C:7]([F:9])(O)[CH:6]=[CH:5][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:3]1.Br[CH2:17][CH2:18][O:19][CH3:20].[I-].[K+].C(=O)([O-])[O-:24].[K+].[K+]>CC(=O)CC>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([O:24][CH2:17][CH2:18][O:19][CH3:20])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[F:9]A mixture of 3,4-difluoro-1,1′-biphenyl-4-ol (0.50 g, 2.43×10−3 mol) of 1-bromo-2-methoxyethane (0.34 g, 2.43×10−3 mol), potassium iodide (0.04 g, 2.43×10−4 mol), potassium carbonate (1.34 g, 9.72×10−3 mol) and butanone (20 cm3) was then heated overnight under reflux. The mixture was filtered to remove inorganic material and the filtrate evaporated down under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane as the eluent and recrystallisation from hexane to give the pure (GC: 100%) desired product (0.15 g 23%).
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