1: potassium carbonate; copper(l) iodide; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 16 h / 20 °C 2: phosphorus tribromide; pyridine / diethyl ether / 16 h / 0 - 20 °C 3: potassium carbonate; copper(l) iodide; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 16 h / 0 - 20 °C 4: phosphorus tribromide; pyridine / diethyl ether / 16 h / 0 - 20 °C View Scheme

N-benzyl-N,N,N-triethylammonium chloride; sodium bromide in dichloromethane; water 6 h; Ambient temperature;

sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride in dichloromethane 0.333333 h; Ambient temperature;

1: 62 percent / Na2CO3; CuI; n-Bu4NCl / dimethylformamide / 24 h / 20 °C 2: 92 percent / H2; quinoline / Pd/CaCO3/Pb / methanol / 2.5 h View Scheme