methanol; potassium carbonate in tetrahydrofuran T=20°C; 1 h;

n-butyllithium in tetrahydrofuran 1.) -78 deg C, 2 h, 2.) room temp., 1 h;

1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 12 h / 65 °C / Inert atmosphere 2: methanol; potassium carbonate / tetrahydrofuran / 1 h / 20 °C View Scheme

1: 96 percent / triphenylphosphine / CH2Cl2 / 1.) 0 deg C, 2.) room temp., 1 h 2: 95.9 percent / n-BuLi / tetrahydrofuran / 1.) -78 deg C, 2 h, 2.) room temp., 1 h View Scheme

1: N-bromosuccinmide 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 12 h / 65 °C / Inert atmosphere 3: methanol; potassium carbonate / tetrahydrofuran / 1 h / 20 °C View Scheme

1: 98.5 percent / Cu2Cl2, N,N,N',N'-tetramethylethylenediamine / 1,2-dimethoxy-ethane / 2 h / 30 - 35 °C 2: 97.5 percent / Na2S*9H2O / dioxane / 20 h / Heating View Scheme