carbon tetrabromide; triphenylphosphine in dichloromethane T=0°C; 0.666667 h;

1: 78 percent / CBr4, PPh3 / CH2Cl2 / 0.67 h / 0 °C 2: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C 3: TsOH / methanol / 2 h / 20 °C 4: 85 percent / CBr4, PPh3 / CH2Cl2 / 0.67 h / 0 °C View Scheme

1: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C 2: TsOH / methanol / 2 h / 20 °C 3: 85 percent / CBr4, PPh3 / CH2Cl2 / 0.67 h / 0 °C View Scheme

1: TsOH / methanol 2: PBr3, Py / diethyl ether View Scheme

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

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

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

1: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C 2: TsOH / methanol / 2 h / 20 °C 3: 67 percent / KOH, K2CO3 / H2O; acetone / 1.5 h / 20 °C 4: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C 5: 5percent aq. NaOH / methanol / 4 h / 20 °C 6: 85.5 percent / H2 / Pd/CaCO3/Pb View Scheme

1: (i) EtMgBr, THF, (ii) /BRN= 1840948/, CuCl, (iii) TsOH, MeOH 2: PBr3, Py / diethyl ether 3: (i) EtMgBr, Et2O, (ii) /BRN= 1841586/, CuCl 4: (i) H2, Lindlar catalyst, EtOH, (ii) /BRN= 102415/, MeOH, Et2O View Scheme

1: (i) EtMgBr, THF, (ii) /BRN= 1840948/, CuCl 2: PBr3, Py / diethyl ether 3: (i) EtMgBr, THF, Et2O, (ii) /BRN= 1817367/, CuCl 4: H2 / Lindlar catalyst / 0 °C / 760 Torr View Scheme