potassium fluoride; hydrogen bromide in DMF (N,N-dimethyl-formamide); water T=20°C; 2.5 h;

1: With sodium carbonate; 1-n-butyl-3-methylimidazolium tetrafluoroborate; tetrakis(triphenylphosphine) palladium(0) in water; N,N-dimethyl-formamide T=110°C; Suzuki-Miyaura cross-coupling; 2 h; 2: With trifluoroacetic acid in dichloromethane 1 h; Further stages.;

1.1: n-butyllithium / tetrahydrofuran; hexane / 1.17 h / -78 °C 1.2: 70 percent / triisopropyl borate / tetrahydrofuran; hexane / -78 - 20 °C 2.1: 48 percent / sodium carbonate / tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane; H2O / 3.5 h / Heating 3.1: KF; aqueous HBr / dimethylformamide / 2.5 h / 20 °C View Scheme

1: 48 percent / sodium carbonate / tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane; H2O / 3.5 h / Heating 2: KF; aqueous HBr / dimethylformamide / 2.5 h / 20 °C View Scheme

NaH-t-AmONa-Ni(OAc)2-bpy-KI 1.) benzene/THF, 63 deg C, 1.75 h; Yield given. Multistep reaction. Yields of byproduct given;