1: With diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide in tetrahydrofuran T=57°C; Sonogashira Coupling; 2: With ethanol; potassium carbonate in tetrahydrofuran

1: 90 percent / diisopropylamine, copper(I) iodide, bis(triphenylphosphine)palladium(II) chloride / tetrahydrofuran / 5 h / 45 °C 2: 96 percent / K2CO3 / ethanol / 2 h / Ambient temperature View Scheme

in toluene T=80°C; 6 h; Title compound not separated from byproducts;

1.1: hydroxylamine hydrochloride; sodium hydroxide; water / ethanol / 3 h / Cooling with ice 1.2: pH 6 2.1: N-chloro-succinimide / N,N-dimethyl-formamide / Cooling with ice; Heating View Scheme

copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran T=20°C; 3.5 h;