N-bromosuccinmide in tetrahydrofuran T=-78°C; 4 h;

tetrabutylammomium bromide; water; copper(ll) bromide in 1,2-dichloro-ethane T=20°C; 1 h;

sodium hydroxide; silica gel; copper(ll) bromide in 1,2-dichloro-ethane T=20°C; 0.25 h;

potassium hydroxide in N,N-dimethyl-formamide T=20°C; 3 h;

1: Br2 / dimethylformamide / 0 - 20 °C 2: 2.66 g / KOH / dimethylformamide / 3 h / 20 °C View Scheme

1: Br2 / dimethylformamide / 0 - 20 °C 2: 2.66 g / KOH / dimethylformamide / 3 h / 20 °C View Scheme

Multistep reaction;

1: palladium diacetate; triphenylphosphine; N,N,N',N,-tetramethylethylenediamine; sodium tetrahydroborate / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere 2: N,N,N',N,-tetramethylethylenediamine; sodium tetrahydroborate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / tetrahydrofuran / 19 h / 20 °C / |Inert atmosphere View Scheme

potassium phosphate; tetrakis(triphenylphosphine) palladium(0) in 1,4-dioxane; water T=90°C; Suzuki-Miyaura Coupling; 6 h;

Multistep reaction;