1: 30 percent / Na / xylene / 120 °C 2: 90 percent / CBr4, Ph3P / acetonitrile / 1.5 h / Ambient temperature 3: 1.) Mg / 1.) THF, 2.) THF, 25 deg C, overnight 4: H2, HCl / 10percent Pd/C / ethanol / 504 h 5: CrO3, pyridine / CH2Cl2 / 0.25 h / 25 °C 6: H2SO4 / 25 °C 7: BBr3 / CH2Cl2 / 3 h / -78 °C 8: NH4Cl, Zn / tetrahydrofuran / 4 h / 60 °C 9: p-TsOH / diethyl ether / 2.5 h / 25 °C View Scheme

1: 90 percent / CBr4, Ph3P / acetonitrile / 1.5 h / Ambient temperature 2: 1.) Mg / 1.) THF, 2.) THF, 25 deg C, overnight 3: H2, HCl / 10percent Pd/C / ethanol / 504 h 4: CrO3, pyridine / CH2Cl2 / 0.25 h / 25 °C 5: H2SO4 / 25 °C 6: BBr3 / CH2Cl2 / 3 h / -78 °C 7: NH4Cl, Zn / tetrahydrofuran / 4 h / 60 °C 8: p-TsOH / diethyl ether / 2.5 h / 25 °C View Scheme