pyridine in dichloromethane T=20°C;

4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide in dichloromethane T=0 - 20°C; 6 h;

sulfuric acid; tert-butyl alcohol T=-20°C;

1: With sec.-butyllithium in tetrahydrofuran; hexane; cyclohexane T=-28°C; 1.52778E-05 h; 2: With tert-butyl alcohol in tetrahydrofuran; hexane; cyclohexane T=-28°C; 0.000638889 h;

1.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 0.67 h / 100 °C / Sealed vial 2.1: 2,2'-azo-bisisobutyronitrile; N-bromosuccinmide / tetrachloromethane / 2 h / 100 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere 3.2: 1 h / 0 - 20 °C 4.1: sodium hydroxide / ethanol / 2 h / 100 °C 4.2: 20 °C / pH ~ 4 5.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.08 h 5.2: 0.5 h / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C View Scheme

1: 95 percent / tetrakis(triphenylphosphine)palladium, 2M aq. sodium carbonate / toluene; ethanol / 4 h / Heating 2: 82 percent / NBS, AIBN / CCl4 / 4.5 h / Heating View Scheme

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in ethanol; toluene 4 h; Heating;

1: tert-butyl 2-bromobenzoate With sec.-butyllithium in tetrahydrofuran; hexane; cyclohexane T=0°C; 2: benzaldehyde in tetrahydrofuran; hexane; cyclohexane T=0°C;

1: tert-butyl 2-bromobenzoate With sec.-butyllithium in tetrahydrofuran; hexane; cyclohexane T=0°C; 2: methyl iodide in tetrahydrofuran; hexane; cyclohexane T=0°C;

1: triethylamine; palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene / dimethyl sulfoxide / 12 h / |Heating 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 3: dicyclohexyl-carbodiimide; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 12 h / 20 °C 4: N-benzyl-cinchoninium bromide; caesium carbonate / toluene / 0 °C View Scheme