Cesium fluoride → 1,2,3-trifluoro-5-((E)-propenyl)benzene

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In nitrogen atmosphere, tetrakistriphenyl-phosphine palladium(0) (4.66 g) and cesium fluoride (21.4 g) were added to a solution mixture of dioxane (95 mL) and water (5 mL) of 1-bromo-3,4,5-trifluorobenzene (8.5 g), trans-1-propen-1-ylboronic acid (4.1 g). The resulting reaction solution was stirred at 80° C. for 5 hr and cooled to room temperature. To the reaction solution, hexane and water were added. The precipitated insoluble matter was removed by filtration, and the organic layer was separated. The obtained organic layer was washed with water, and the insoluble matter was removed by filtration again. The organic layer was separated. The obtained organic layer was washed with water and then with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: hexane) to give 5.83 g of the title compound. The physical property values of this compound were as follows:

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