Triethylamine → Methyl 4-[(4-ethoxyphenyl)ethynyl]-2-fluorobenzoate

Participants

Reaction Steps

To methyl 4-bromo-2-fluorobenzoate (1.29 g, 5.54 mmol) in THF (10 mL)-triethylamine (5 mL) solvent were added 1-ethoxy-4-ethynylbenzene (1.24 mL, 8.30 mmol), copper(I) iodide (106 mg, 0.544 mmol) and bis(triphenylphosphine)palladium(II) chloride (195 mg, 0.277 mmol), and the mixture was stirred under an argon stream at room temperature for 15 min. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=97:3 to 17:3) to give the title compound (1.38 g, yield 84%) as an oil.

Provenance & Evidence