1: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C 2: 5percent aq. NaOH / methanol / 4 h / 20 °C 3: 85.5 percent / H2 / Pd/CaCO3/Pb View Scheme

1: (i) EtMgBr, THF, Et2O, (ii) /BRN= 1817367/, CuCl 2: H2 / Lindlar catalyst / 0 °C / 760 Torr View Scheme

Multi-step reaction with 5 steps 1: phosphorus tribromide; pyridine / diethyl ether / 16 h / 0 - 20 °C2: potassium carbonate; copper(l) iodide; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 16 h / 0 - 20 °C3: phosphorus tribromide; pyridine / diethyl ether / 16 h / 0 - 20 °C4: potassium carbonate; copper(l) iodide; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 16.5 h / 0 - 20 °C5: phosphorus tribromide; pyridine / dichloromethane / 16 h / 0 - 20 °C