1.1: 95 percent / K2CO3 / acetonitrile / 2.5 h / 0 - 20 °C 2.1: BuLi; TMEDA / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: tetrahydrofuran; hexane / 4 h / -78 - 20 °C 3.1: NH4Cl / benzene / 4 h / Heating 4.1: 84 percent / conc. aq. HCl / tetrahydrofuran; methanol / 24 h / 20 °C View Scheme

1.1: 1H-imidazole / N,N-dimethyl-formamide / 21.5 h / 20 °C / |Inert atmosphere 2.1: dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; caesium carbonate; palladium diacetate / toluene / 28 h / 100 °C / |Inert atmosphere 3.1: copper diacetate; 2,2,2-trimethylacetic acid; palladium diacetate / 3 h / 110 °C / |Microwave irradiation; |Inert atmosphere 4.1: boron tribromide / dichloromethane / 14.8 h / -78 - 20 °C / |Inert atmosphere 5.1: copper dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 29 h / 20 °C / |Inert atmosphere 5.2: 23 h / |Reflux; |Inert atmosphere 6.1: tetrabutyl ammonium fluoride / N,N-dimethyl-formamide; tetrahydrofuran / 0.17 h / -10 °C / |Inert atmosphere View Scheme

1: 5-bromo-2-methylphenol With n-butyllithium in tetrahydrofuran; hexanes T=-78°C; 0.5 h; 2: chloro-trimethyl-silane in tetrahydrofuran; hexanes T=-78°C; 1.5 h;

1.1: sodium hydride / tetrahydrofuran; mineral oil / 4 h / Reflux 2.1: n-butyllithium / tetrahydrofuran / -20 °C 2.2: -78 - -40 °C 3.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0 °C View Scheme