1: 1.) EtMgBr / 2.) CuCl / 1.) THF, 50 deg C, 30 min; 2.) THF, 50-55 deg C, 2 h 2: 82 percent / acetyl chloride, stannic chloride / CH2Cl2 / 0.25 h / 10 - 15 °C View Scheme

1.1: magnesium / tetrahydrofuran / 15 - 22 °C 1.2: 1 h 2.1: potassium hydroxide / methanol / 1 h View Scheme

1.1: magnesium / tetrahydrofuran / 3.5 h / |Inert atmosphere 1.2: 16 h / 25 °C 2.1: potassium hydroxide / methanol / 25 °C 3.1: palladium diacetate; 1,4-di(diphenylphosphino)-butane; potassium carbonate / acetonitrile / 1 h / |Inert atmosphere; |Large scale 3.2: 16 h / 80 °C / |Large scale 4.1: dichloro bis(acetonitrile) palladium(II) / acetonitrile / 20 - 80 °C / |Inert atmosphere; |Large scale View Scheme

1.1: magnesium / tetrahydrofuran / 3.5 h / 10 - 15 °C 1.2: 17.5 h / 25 °C / Cooling with ice 1.3: 5 - 25 °C 2.1: potassium hydroxide / methanol / 5 - 25 °C 2.2: 0.5 h View Scheme

1.1: magnesium / tetrahydrofuran / 3.5 h / |Inert atmosphere 1.2: 16 h / 25 °C 2.1: potassium hydroxide / methanol / 25 °C 3.1: palladium diacetate; 1,4-di(diphenylphosphino)-butane; potassium carbonate / acetonitrile / 1 h / |Inert atmosphere; |Large scale 3.2: 16 h / 80 °C / |Large scale 4.1: dichloro bis(acetonitrile) palladium(II) / acetonitrile / 20 - 80 °C / |Inert atmosphere; |Large scale 5.1: triethylamine / dichloromethane / 0 - 20 °C 6.1: 5 palladium on charcoal; hydrogen / tetrahydrofuran / 50 °C / 2250.23 Torr / |Inert atmosphere; |Sealed tube View Scheme

copper bronze; water; copper; triethylamine; copper(l) iodide in tetrahydrofuran T=60 - 70°C; 4 h;

1: 75 percent / Mg / tetrahydrofuran / Ambient temperature 2: 85 percent / AgNO3, KCN / Ambient temperature 3: 100 percent / H2, quinoline / Pd-BaSO4 View Scheme

ethylmagnesium bromide; copper(l) chloride

1: 1.) EtMgBr / 2.) CuCl / 1.) THF, 50 deg C, 30 min; 2.) THF, 50-55 deg C, 2 h 2: 80 percent / potassium hydroxide / methanol / 16 h / 0 °C View Scheme

1: 1.) EtMgBr / 2.) CuCl / 1.) THF, 50 deg C, 30 min; 2.) THF, 50-55 deg C, 2 h 2: 77 percent / potassium hydroxide / methanol / 16 h / 0 °C View Scheme