triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide in N,N-dimethyl-formamide T=20°C; 4 h; Inert atmosphereCooling with iceSealed vessel;

1: triphenyl-methyl-phosphonium iodide With n-butyllithium in tetrahydrofuran T=0°C; Wittig Olefination; 0.25 h; Inert atmosphere; 2: 2-bromo-4-fluoro-benzaldehyde in tetrahydrofuran 2.25 h; Inert atmosphereCooling with ice;

potassium carbonate in N,N-dimethyl-formamide T=100°C; 17 h; Inert atmosphere;

1.1: toluene-4-sulfonic acid / toluene / 4 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 4 h / 65 °C / Cooling; Inert atmosphere 3.1: n-butyllithium; tri-isopropoxy-borane / tetrahydrofuran / -80 - 20 °C / Inert atmosphere 3.2: 2 h 4.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C 5.1: palladium 10 on activated carbon; hydrogen / methanol / 20 °C View Scheme

1: in diethyl ether T=0°C; 2.33333 h; Inert atmosphere; 2: With water; ammonium chloride in diethyl ether

1: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide T=80°C; Inert atmosphere; 2: With methanol; potassium carbonate T=20°C; 0.25 h;

1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / 0.08 h / 20 °C / |Inert atmosphere 1.2: 5 h / 80 °C / |Inert atmosphere 2.1: potassium carbonate; methanol / 5 h / 20 °C View Scheme

1.1: toluene-4-sulfonic acid / toluene / 24 h / Reflux; Inert atmosphere 2.1: tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere 2.2: -78 - 0 °C / Inert atmosphere 2.3: 0 °C / Inert atmosphere 3.1: hydrogenchloride; water / 1,4-dioxane / 3 h / 20 °C / Inert atmosphere View Scheme