bis(cyclopentadienyl)zirconium monomethylmonochloride; iodine; tert.-butyl lithium 1) THF, -78 to 45 deg C, 2) CH2Cl2, 0 deg C; Yield given. Multistep reaction;

1: Fe, HCl / ethanol 2: NaHCO3 / dimethylformamide 3: 1) t-BuLi, Cp2Zr(CH3)Cl, 2) I2 / 1) THF, -78 to 45 deg C, 2) CH2Cl2, 0 deg C View Scheme

1: NaHCO3 / dimethylformamide 2: 1) t-BuLi, Cp2Zr(CH3)Cl, 2) I2 / 1) THF, -78 to 45 deg C, 2) CH2Cl2, 0 deg C View Scheme

1: 88 percent / CuBr2, t-BuONO / acetonitrile 2: Fe, HCl / ethanol 3: NaHCO3 / dimethylformamide 4: 1) t-BuLi, Cp2Zr(CH3)Cl, 2) I2 / 1) THF, -78 to 45 deg C, 2) CH2Cl2, 0 deg C View Scheme

boron tribromide in dichloromethane

1.1: acetonitrile / 4 h / |Reflux; |Inert atmosphere 2.1: AlCl3, aluminium chloride; lithium aluminium tetrahydride / diethyl ether / 0.33 h / 0 °C / |Inert atmosphere 3.1: triethylamine / 1,2-dichloro-ethane / 10 h / 20 °C / |Inert atmosphere 4.1: sodium iodide / acetone / 5 h / |Inert atmosphere; |Reflux 5.1: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C / |Inert atmosphere; |Schlenk technique 6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 0.33 h / 0 °C / |Inert atmosphere 7.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / |Inert atmosphere 8.1: water; sodium hydroxide / methanol / 0.5 h / |Reflux; |Inert atmosphere 9.1: Fremy’s salt / acetone / 0.33 h / 0 - 20 °C / pH 6.86 10.1: acetone / 0.5 h / 60 °C / |Sealed tube; |Inert atmosphere 10.2: 7 h / 70 °C / |Sealed tube; |Inert atmosphere View Scheme

1.1: acetonitrile / 4 h / |Reflux; |Inert atmosphere 2.1: AlCl3, aluminium chloride; lithium aluminium tetrahydride / diethyl ether / 0.33 h / 0 °C / |Inert atmosphere 3.1: triethylamine / 1,2-dichloro-ethane / 10 h / 20 °C / |Inert atmosphere 4.1: sodium iodide / acetone / 5 h / |Inert atmosphere; |Reflux 5.1: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; hexane / 0.67 h / -78 - 0 °C / |Inert atmosphere 5.2: 0.5 h / -78 - 0 °C / |Inert atmosphere 6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 0.33 h / 0 - 20 °C / |Inert atmosphere 7.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / |Inert atmosphere 8.1: water; sodium hydroxide / methanol / 0.5 h / |Reflux; |Inert atmosphere 9.1: Fremy’s salt / acetone / 0.33 h / 0 - 20 °C / pH 6.86 / |Inert atmosphere 10.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C / |Inert atmosphere 11.1: ammonium chloride / ethanol / 0.33 h / |Inert atmosphere; |Reflux View Scheme

1: acetonitrile / 4 h / |Reflux; |Inert atmosphere 2: AlCl3, aluminium chloride; lithium aluminium tetrahydride / diethyl ether / 0.33 h / 0 °C / |Inert atmosphere 3: triethylamine / 1,2-dichloro-ethane / 10 h / 20 °C / |Inert atmosphere 4: sodium iodide / acetone / 5 h / |Inert atmosphere; |Reflux 5: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C / |Inert atmosphere; |Schlenk technique 6: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 0.33 h / 0 °C / |Inert atmosphere 7: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / |Inert atmosphere 8: water; sodium hydroxide / methanol / 0.5 h / |Reflux; |Inert atmosphere 9: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 0 °C / |Inert atmosphere 10: salenCo(II); oxygen / N,N-dimethyl-formamide / 1 h / 20 °C / |Inert atmosphere 11: ammonium chloride / methanol / 13 h / 20 °C / |Inert atmosphere View Scheme