potassium carbonate in methanol T=20°C;

1: 2,2'-azo-bisisobutyronitrile; N-bromosuccinmide / tetrachloromethane / 4 h / |Reflux 2: copper dilithium tetrachloride / tetrahydrofuran; diethyl ether / 2 h / 0 - 20 °C 3: potassium carbonate / methanol / 20 °C View Scheme

1: copper dilithium tetrachloride / tetrahydrofuran; diethyl ether / 2 h / 0 - 20 °C 2: potassium carbonate / methanol / 20 °C View Scheme

1.1: pyridine / 6 h / 0 °C 2.1: copper(l) iodide; methyllithium / tetrahydrofuran; diethyl ether / 1 h / -78 °C 2.2: 0.17 h / 20 °C 3.1: 2,2'-azo-bisisobutyronitrile; N-bromosuccinmide / tetrachloromethane / 4 h / |Reflux 4.1: copper dilithium tetrachloride / tetrahydrofuran; diethyl ether / 2 h / 0 - 20 °C 5.1: potassium carbonate / methanol / 20 °C View Scheme

1.1: copper(l) iodide; methyllithium / tetrahydrofuran; diethyl ether / 1 h / -78 °C 1.2: 0.17 h / 20 °C 2.1: 2,2'-azo-bisisobutyronitrile; N-bromosuccinmide / tetrachloromethane / 4 h / |Reflux 3.1: copper dilithium tetrachloride / tetrahydrofuran; diethyl ether / 2 h / 0 - 20 °C 4.1: potassium carbonate / methanol / 20 °C View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine; thionyl chloride / ethylene glycol dimethyl ether / 3.5 h 2.1: pyridine / 6 h / 0 °C 3.1: copper(l) iodide; methyllithium / tetrahydrofuran; diethyl ether / 1 h / -78 °C 3.2: 0.17 h / 20 °C 4.1: 2,2'-azo-bisisobutyronitrile; N-bromosuccinmide / tetrachloromethane / 4 h / |Reflux 5.1: copper dilithium tetrachloride / tetrahydrofuran; diethyl ether / 2 h / 0 - 20 °C 6.1: potassium carbonate / methanol / 20 °C View Scheme