1: 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane With dimethyl zinc; Mg(O-t-Bu)2 in 1,4-dioxane; hexane T=0 - 20°C; 0.5 h; Schlenk techniqueGloveboxInert atmosphere; 2: 2-iodo-3-bromoanisole in 1,4-dioxane; hexane T=20 - 120°C; 24 h; Schlenk techniqueGloveboxInert atmosphere; 3: With water in 1,4-dioxane; hexane T=20°C; 0.0833333 h; Schlenk techniqueGloveboxInert atmosphere; regioselective reaction;

boron tribromide in dichloromethane T=-78°C;

1.1: boron tribromide / dichloromethane / -78 - 20 °C 1.2: 0 - 20 °C 2.1: sodium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere 3.1: sodium hydroxide / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 4.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diethylamine / N,N-dimethyl-formamide / 3 h / 40 °C / Inert atmosphere 5.1: sodium hydroxide / N,N-dimethyl-formamide / 5 h / 140 °C / Inert atmosphere View Scheme

1: With tBu2Zn(TMP)Li in tetrahydrofuran T=-30°C; 12 h; 2: With iodine in tetrahydrofuran T=20°C; Further stages.;

1.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 84 percent / I2 / tetrahydrofuran; hexane / -78 - 20 °C 2.1: NaOH / ethanol / Heating 3.1: 2.50 g / K2CO3 / acetonitrile / Heating View Scheme

1: NaOH / ethanol / Heating 2: 2.50 g / K2CO3 / acetonitrile / Heating View Scheme

potassium carbonate in acetonitrile Heating;

1: 2-iodo-3-bromoanisole With tert.-butyl lithium in tetrahydrofuran; pentane T=-100°C; 0.75 h; 2: ortho-dibromobenzene in tetrahydrofuran; pentane T=-100 - 25°C; 14 h; Further stages.;