N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile in tetrachloromethane 2 h; Heating;

1.1: tetrahydrofuran; diethyl ether / 1.5 h / -78 - 0 °C 1.2: 85 percent / MeI / tetrahydrofuran; diethyl ether / 0.17 h / 0 °C 2.1: 78 percent / N-bromosuccinimide; AIBN / CCl4 / 2 h / Heating View Scheme

1: 89 percent / DMAP; thionyl chloride / 1,2-dimethoxy-ethane / 3 h 2: 75 percent / N-bromosuccinimide; benzoyl peroxide / CCl4 / 15 h / Heating View Scheme

1: With 4-(N,N-dimethlyamino)pyridine; thionyl chloride 2: With N-bromosuccinmide; dibenzoyl peroxide in tetrachloromethane Heating;

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 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 View Scheme

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