1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 10 h / 20 °C 2.1: AlCl3, aluminium chloride / dichloromethane / 1 h / -5 - 20 °C / |Inert atmosphere 2.2: 2 h / -5 - 0 °C / |Inert atmosphere 3.1: AlCl3, aluminium chloride; sodium tetrahydroborate / tetrahydrofuran / 18 h / 5 - 20 °C / |Inert atmosphere 4.1: boron tribromide / dichloromethane / -10 - 0 °C / |Inert atmosphere 5.1: triethylamine / acetonitrile / 2 h / 5 - 15 °C 6.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.5 h / -65 °C / |Inert atmosphere 6.2: 3 h / -65 - -55 °C 6.3: 16 h / 20 - 25 °C 7.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 2 h / -30 - -10 °C / |Inert atmosphere 8.1: caesium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 12 h / 40 °C / |Inert atmosphere View Scheme

bis-triphenylphosphine-palladium(II) chloride; sodium carbonate in ethylene glycol dimethyl ether; ethanol; water T=50°C; Suzuki-Miyaura coupling; 15 h; Inert atmosphere;

dimethylsulfide; borane in tetrahydrofuran T=20°C; 24 h;

sodium tetrahydroborate; base soluble Sn(IV) reagent; V-501 in potassium hydroxide T=90°C; Yield given;

sulfuric acid 72 h; Heating;

in methanol; dichloromethane; N,N-dimethyl-formamide

1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 12 h / 20 °C / Inert atmosphere 2: dichloromethane / 1.17 h / 0 - 20 °C View Scheme

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in ethanol; water; N,N-dimethyl-formamide T=100°C; Inert atmosphere;

potassium carbonate; CuPy2Cl2 T=75°C; 0.333333 h; microwave irradiation;

1: N-methyl-O-methylhydroxyamine hydrochloride With triethylamine in dichloromethane 16 h; 2: 5-bromo-2-chloro-benzoic acid With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride in dichloromethane