Under a nitrogen atmosphere, a mixture of 1-bromo-3-(p-chlorophenyl)-1-fluoro-4-methyl-1-pentene, (E)- and (Z)- (0,9 g, 3,1 mmol), tetrakis(triphenylphosphine)-palladium(0) (0,25 g, 0,22 mmol), and N,N-dimethyl-formamide (20 ml) was treated with 5 ml of a 3-phenoxybenzylzinc bromide solution (prepared from 3-phenoxybenzyl bromide (1,3 g, 5,4 mmol) and Rieke zinc (4 ml of a 1,5 molar solution in tetrahydrofuran), and tetrahydrofuran 2.0 ml). The resultant reaction mixture was stirred at room temperature for one hour, treated with an additional 5 ml of the 3-phenoxybenzylzinc bromide solution, stirred at room temperature, and poured into 2 N hydrochloric acid solution. The resultant aqueous mixture was extracted with diethyl ether. The organic extract was dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a residue. Column chromatography of the residue using silica gel, and 100:1 and 200:1 hexane/ethyl acetate solutions gave the title product (0,35 g) predominately in the (Z)-configuration.
