methanol; potassium hydroxide in tetrahydrofuran T=20°C; 1 h; Inert atmosphere;

potassium carbonate in methanol 20 h; Ambient temperature;

1: 95.1 percent / N-bromosuccinimide / CHCl3; acetic acid / 4 h / 70 °C 2: 92.7 percent / dichlorobis(benzonitrile)palladium(II), PPh3, CuI / various solvent(s) / 4 h / 70 °C 3: 95.8 percent / K2CO3 / methanol / 4 h / Ambient temperature View Scheme

1: 92.7 percent / dichlorobis(benzonitrile)palladium(II), PPh3, CuI / various solvent(s) / 4 h / 70 °C 2: 95.8 percent / K2CO3 / methanol / 4 h / Ambient temperature View Scheme

1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine / toluene / 48 h / 20 °C / Inert atmosphere 2: methanol; potassium hydroxide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere View Scheme