N-benzyl-N,N,N-trimethyl-ammonium chloride; zinc(II) chloride in N,N-dimethyl-formamide T=20°C; 1.5 h; BrominationInert atmosphere;

1: With N-bromosuccinmide in N,N-dimethyl-formamide T=0 - 20°C; Inert atmosphereDarkness; 2: With water in N,N-dimethyl-formamide T=0°C; Inert atmosphere;

1: potassium iodide; potassium hydroxide / dimethyl sulfoxide / 16 h / 0 - 20 °C 2: N-bromosuccinmide / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere; Darkness View Scheme

1.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C 1.2: -78 - 20 °C 2.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C 2.2: -78 - 20 °C 3.1: pyridinium chlorochromate / dichloromethane / 12 h / 20 °C 4.1: copper / N,N-dimethyl-formamide / 15 h / Reflux 5.1: hydrazine hydrate; potassium hydroxide / ethylene glycol / 8 h / 180 °C / Inert atmosphere 6.1: potassium iodide; potassium hydroxide / dimethyl sulfoxide / 16 h / 0 - 20 °C 7.1: N-bromosuccinmide / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere; Darkness View Scheme

1: hydrazine hydrate; potassium hydroxide / ethylene glycol / 8 h / 180 °C / Inert atmosphere 2: potassium iodide; potassium hydroxide / dimethyl sulfoxide / 16 h / 0 - 20 °C 3: N-bromosuccinmide / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere; Darkness View Scheme

1.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C 1.2: -78 - 20 °C 2.1: pyridinium chlorochromate / dichloromethane / 12 h / 20 °C 3.1: copper / N,N-dimethyl-formamide / 15 h / Reflux 4.1: hydrazine hydrate; potassium hydroxide / ethylene glycol / 8 h / 180 °C / Inert atmosphere 5.1: potassium iodide; potassium hydroxide / dimethyl sulfoxide / 16 h / 0 - 20 °C 6.1: N-bromosuccinmide / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere; Darkness View Scheme

1: pyridinium chlorochromate / dichloromethane / 12 h / 20 °C 2: copper / N,N-dimethyl-formamide / 15 h / Reflux 3: hydrazine hydrate; potassium hydroxide / ethylene glycol / 8 h / 180 °C / Inert atmosphere 4: potassium iodide; potassium hydroxide / dimethyl sulfoxide / 16 h / 0 - 20 °C 5: N-bromosuccinmide / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere; Darkness View Scheme

1: copper / N,N-dimethyl-formamide / 15 h / Reflux 2: hydrazine hydrate; potassium hydroxide / ethylene glycol / 8 h / 180 °C / Inert atmosphere 3: potassium iodide; potassium hydroxide / dimethyl sulfoxide / 16 h / 0 - 20 °C 4: N-bromosuccinmide / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere; Darkness View Scheme

1.1: quinoline; copper / 0.67 h / 237 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / 0 - 20 °C / Inert atmosphere 2.2: 4 h / 0 - 30 °C / Inert atmosphere 3.1: N-benzyl-N,N,N-trimethyl-ammonium chloride; zinc(II) chloride / N,N-dimethyl-formamide / 1.5 h / 20 °C / Bromination; Inert atmosphere View Scheme