[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([O:11][CH2:12][O:13][CH3:14])=[C:6](Br)[CH:5]=1.[CH3:17][Zn]C.CO>O1CCOCC1.CCOCC>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:5]=[C:6]([CH3:17])[C:7]([O:11][CH2:12][O:13][CH3:14])=[C:8]([F:10])[CH:9]=1To a solution of 3-bromo-5-fluoro-4-methoxymethoxybenzoic acid methyl ester (301 mg) and (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II)(42 mg) in dioxane (5 mL) was added dimethylzinc (2M toluene solution) (2.1 mL). The mixture was stirred at 120° C. for 3 hours under heating and then cooled down to 0° C., and methanol (0.3 mL) was added thereto. The mixture was diluted with ether, washed with 1M hydrochloric acid and saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=50:1, v/v) to give the title compound (197 mg).
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