1: 1-fluoro-2-(4-iodophenoxy)-benzene With n-butyllithium in tetrahydrofuran; water T=-78 - 20°C; pH=2 - 4; 0.166667 h; Inert atmosphere; 2: tri-isopropoxy-borane in tetrahydrofuran; water

1: With n-butyllithium in tetrahydrofuran T=-78°C; 0.166667 h; Inert atmosphere; 2: With tri-isopropoxy-borane in tetrahydrofuran T=-78 - 20°C; 0.166667 h; Inert atmosphere; 3: With water; ammonium chloride in tetrahydrofuran

1.1: sodium hydride / copper(l) chloride / N,N-dimethyl-formamide; mineral oil / 5 h / 100 °C 2.1: ammonium chloride; iron / water; methanol / 1.33 h / 80 °C / Reflux 3.1: hydrogenchloride; sodium nitrite / 0.5 h / 0 °C 3.2: 0.33 h / 0 °C 3.3: 1 h / 20 °C 4.1: n-butyllithium / water; tetrahydrofuran / 0.17 h / -78 - 20 °C / pH 2 - 4 / Inert atmosphere View Scheme

1.1: sodium hydride / copper(l) chloride / N,N-dimethyl-formamide; mineral oil / 5 h / 100 °C 2.1: ammonium chloride; iron / water; methanol / 1.33 h / 80 °C / Reflux 3.1: hydrogenchloride; sodium nitrite / 0.5 h / 0 °C 3.2: 0.33 h / 0 °C 3.3: 1 h / 20 °C 4.1: n-butyllithium / water; tetrahydrofuran / 0.17 h / -78 - 20 °C / pH 2 - 4 / Inert atmosphere View Scheme

1.1: hydrogenchloride; sodium nitrite / 0.5 h / 0 °C 1.2: 0.33 h / 0 °C 1.3: 1 h / 20 °C 2.1: n-butyllithium / water; tetrahydrofuran / 0.17 h / -78 - 20 °C / pH 2 - 4 / Inert atmosphere View Scheme