sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethanol Suzuki cross-coupling; 12 h; Heating;

1: With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 30 h; 2: With tri-isopropoxy-borane in tetrahydrofuran; hexane T=-78 - 20°C; 2 h; Further stages.;

1.1: conc. H2SO4 / 80 °C 2.1: 80 percent / Br2 / CCl4 / 0 - 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 30 h / -78 °C 3.2: triisopropyl borate / tetrahydrofuran; hexane / 2 h / -78 - 20 °C View Scheme

1.1: 80 percent / Br2 / CCl4 / 0 - 20 °C 2.1: BuLi / tetrahydrofuran; hexane / 30 h / -78 °C 2.2: triisopropyl borate / tetrahydrofuran; hexane / 2 h / -78 - 20 °C View Scheme

1.1: BuLi / tetrahydrofuran; hexane / -40 °C 1.2: tetrahydrofuran; hexane / -40 - 20 °C 2.1: conc. H2SO4 / 80 °C 3.1: 80 percent / Br2 / CCl4 / 0 - 20 °C 4.1: BuLi / tetrahydrofuran; hexane / 30 h / -78 °C 4.2: triisopropyl borate / tetrahydrofuran; hexane / 2 h / -78 - 20 °C View Scheme