1: 2,7-dibromo-9,9-di-n-octylfluorene With n-butyllithium in tetrahydrofuran; hexane T=-78 - 0°C; 0.616667 h; 2: 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in tetrahydrofuran; hexane T=-78 - 20°C; 30 h;

1: 2,7-dibromo-9,9-bis(4-n-hexylphenyl)fluorene With n-butyllithium in tetrahydrofuran; hexane T=-78 - -70°C; 6 h; Inert atmosphere; 2: 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in tetrahydrofuran; hexane T=-70°C; Inert atmosphere; 3: With hydrogenchloride in tetrahydrofuran; diethyl ether; hexane T=-30 - 20°C; Inert atmosphere;

1: 2,7-dibromo-9,9-di-n-octylfluorene With n-butyllithium T=-78°C; 2: iPrB(pinacolate)

1.1: n-butyllithium / tetrahydrofuran / -78 - 20 °C 1.2: 30.8 g / tetrahydrofuran / -78 - 20 °C 2.1: 90 percent / FeCl3; Br2 / CHCl3 / 3 h / 0 - 20 °C 3.1: n-butyllithium / tetrahydrofuran / 0.25 h / -78 - 20 °C 3.2: tetrahydrofuran / 24 h / -78 - 20 °C View Scheme

1: 85 percent / aq. NaOH / dimethylsulfoxide 2: 79 percent / BuLi / -78 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran / -78 - 20 °C 1.2: 30.8 g / tetrahydrofuran / -78 - 20 °C 2.1: 90 percent / FeCl3; Br2 / CHCl3 / 3 h / 0 - 20 °C 3.1: n-butyllithium / tetrahydrofuran / 0.25 h / -78 - 20 °C 3.2: tetrahydrofuran / 24 h / -78 - 20 °C View Scheme

1.1: 90 percent / FeCl3; Br2 / CHCl3 / 3 h / 0 - 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.25 h / -78 - 20 °C 2.2: tetrahydrofuran / 24 h / -78 - 20 °C View Scheme

(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate in dimethyl sulfoxide

1: sodium hydroxide / dimethyl sulfoxide 2: n-butyllithium / tetrahydrofuran / -78 °C View Scheme