1-Fluoro-3-iodobenzene → Tert-butyl 3-(3-fluorophenyl)prop-2-ynoate

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Reaction Conditions

Reaction Steps

A dry, argon-filled Schlenk tube with a magnetic stirrer bar and septum is initially charged with tert-butyl prop-2-ynoate (70 mg, 0.56 mmol) in anhydrous THF (2 ml). After adding (TMP)2Zn.MgCl2 (2.2 ml, 1.2 mmol) at 25° C., the mixture is stirred for 30 min, then a solution of 1-fluoro-3-iodobenzene (160 mg, 0.72 mmol), tetrakis(triphenylphosphine)palladium(0) (33 mg, 5 mol %) in anhydrous THF (2 ml) is added dropwise and the mixture is stirred at 25° C. overnight. For workup, the mixture is diluted with aqueous sat. NH4Cl solution (30 ml) and extracted with ethyl acetate (3×30 ml). After the combined organic phases have been dried over Na2SO4, the solvent has been distilled off and purification has been effected by column chromatography on silica gel (heptane:ethyl acetate), the desired compound (91 mg, 75% of theory) was obtained as a colourless oil.

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