[CH3:1][C:2](C)([O-])C.[K+].[Cl:7][C:8]1[C:15]([CH:16]2[O:20][CH2:19][CH2:18][O:17]2)=[CH:14][CH:13]=[C:12]([F:21])[C:9]=1[CH:10]=O>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.O1CCCC1.[Cl-].[Na+].O>[Cl:7][C:8]1[C:9]([CH:10]=[CH:1][CH3:2])=[C:12]([F:21])[CH:13]=[CH:14][C:15]=1[CH:16]1[O:20][CH2:19][CH2:18][O:17]1
To a solution of ethyltriphenylphosphonium bromide (3.43 g) in tetrahydrofuran (15 mL) was added potassium tert-butoxide (1.31 g) at 0° C., and the mixture was stirred at room temperature for 1 hr. Successively, 2-chloro-3-(1,3-dioxolan-2-yl)-6-fluorobenzaldehyde (1.35 g) was added to the mixture, and the mixture was stirred for 2.5 hr. To the reaction mixture was added saturated brine, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give crude 2-{2-chloro-4-fluoro-3-[prop-1-en-1-yl]phenyl}-1,3-dioxolane (1.41 g).
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