1: 99 percent / imidazole / dimethylformamide / 3 h / 35 °C 2: 1.) Cp2Zr(Cl)H, 2.) I2 / 1.) benzene, 40 deg C, 2.) hexane, 5 min 3: 95 percent / <(Ph3P)4Pd>, n-BuNH2, CuI / benzene / 0.5 h 4: 85 percent / AgNO3, KCN / aq. ethanol / 0.5 h / 30 °C 5: 1.) Cp2Zr(Cl)H, 2.) I2 / 1.) THF, 35 deg C, 15 min 6: 78 percent / n-butylamine, copper iodide / Pd<P(Ph3)>4 / benzene / 3 h / Ambient temperature 7: Bu4NF / tetrahydrofuran / 2 h / Ambient temperature 8: 85 percent 9: 65 percent / Zn, MeOH / H2O / 5 h / 30 °C 10: 95 percent / K2CO3 / methanol; H2O / Ambient temperature View Scheme

Multi-step reaction with 9 steps 1: 99 percent / imidazole / dimethylformamide / 3 h / 35 °C2: 1.) Cp2Zr(Cl)H, 2.) I2 / 1.) benzene, 40 deg C, 2.) hexane, 5 min3: 95 percent / <(Ph3P)4Pd>, n-BuNH2, CuI / benzene / 0.5 h4: 85 percent / AgNO3, KCN / aq. ethanol / 0.5 h / 30 °C5: 1.) Cp2Zr(Cl)H, 2.) I2 / 1.) THF, 35 deg C, 15 min6: 78 percent / n-butylamine, copper iodide / Pd<P(Ph3)>4 / benzene / 3 h / Ambient temperature7: Bu4NF / tetrahydrofuran / 2 h / Ambient temperature8: 85 percent9: 65 percent / Zn, MeOH / H2O / 5 h / 30 °C  

With  potassium tert-butylate in  tetrahydrofuran T=-78 - 0°C;   

With  potassium carbonate in  methanol; water T=25°C; 2 h;   

Multi-step reaction with 2 steps 1: 94 percent / Na-methanolate / methanol / 3 h / Ambient temperature2: 86 percent / K-tert-butoxide / 1,2-dimethoxy-ethane