zirconocene dichloride in tetrahydrofuran T=20°C; Inert atmosphere;

1.1: s-BuLi; TMEDA / cyclohexane; hexane; tetrahydrofuran / 2 h / -78 °C 1.2: 84 percent / 1,2-dibromo-1,1,2,2-tetrachloroethane / tetrahydrofuran; hexane; cyclohexane / -78 - 20 °C 2.1: 75 percent / NaOH / ethanol / Heating View Scheme

1.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C 2.1: sodium hydroxide / ethanol / Reflux 3.1: sodium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 3.2: 2 h / 20 °C / Inert atmosphere 4.1: sodium hydroxide / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 5.1: hydrogenchloride / ethanol; water / Reflux View Scheme

1.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C 2.1: sodium hydroxide / ethanol / Reflux 3.1: sodium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 3.2: 2 h / 20 °C / Inert atmosphere 4.1: sodium hydroxide / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 5.1: hydrogenchloride / ethanol; water / Reflux View Scheme

1: (4-methoxyphenyl)-boronic acid T=75°C; 4 h; dehydrationvacuum; 2: 3-fluorophenyl diethylcarbamate With potassium phosphate; NiCl2(PCy3)2; PCy3∙HBF4 in o-xylene T=150°C; Suzuki-Miyaura coupling; 5 h; Inert atmosphere;

potassium phosphate; Ni(PCy3)2Cl2; PCy3∙HBF4 in o-xylene T=150°C; Suzuki-Miyaura cross-coupling; 5 - 20 h; Inert atmosphere;

1: With N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium in tetrahydrofuran; hexane; cyclohexane T=-78°C; 2 h; 2: With iodine in tetrahydrofuran; hexane; cyclohexane T=-78 - 20°C;

1: With N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium in tetrahydrofuran; hexane; cyclohexane T=-78°C; 2 h; 2: With 1,2-dibromo-1,1,2,2-tetrachloroethane in tetrahydrofuran; hexane; cyclohexane T=-78 - 20°C;

1: With N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium in tetrahydrofuran; hexane; cyclohexane T=-78°C; 2 h; 2: With 1,2,2-trichloro-1,1,2-trichloro-ethane in tetrahydrofuran; hexane; cyclohexane T=-78 - 20°C;

1.1: s-BuLi; TMEDA / cyclohexane; hexane; tetrahydrofuran / 2 h / -78 °C 1.2: 88 percent / iodine / tetrahydrofuran; hexane; cyclohexane / -78 - 20 °C 2.1: 66 percent / NaOH / ethanol / Heating View Scheme