1: With hydrogenchloride; NH4BF4; sodium nitrite in water 0.583333 h; 2: With 18-crown-6 ether; potassium acetate in chloroform; water T=20°C; 2 h; Product distribution / selectivity;

diazomethane in tetrahydrofuran; diethyl ether T=0°C; 1 h;

sulfuric acid T=60°C; Inert atmosphere;

1.1: hydrogen / palladium on activated charcoal / methanol / 20 °C 2.1: hydrogenchloride; sodium nitrite; NH4BF4 / water / 0.58 h 2.2: 2 h / 20 °C View Scheme

1.1: thionyl chloride / 1 h / 0 - 80 °C 2.1: hydrogen / palladium on activated charcoal / methanol / 20 °C 3.1: hydrogenchloride; sodium nitrite; NH4BF4 / water / 0.58 h 3.2: 2 h / 20 °C View Scheme

triethylamine in tetrahydrofuran; N,N-dimethyl-formamide T=20°C; 1 h;

1.1: thionyl chloride / dichloromethane / 3 h / 80 °C 2.1: hydrogenchloride; sodium nitrite; NH4BF4 / water / 0.58 h 2.2: 2 h / 20 °C View Scheme

1.1: sodium hydroxide; N-bromosuccinmide / N,N-dimethyl-formamide / 1 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 - 20 °C / |Inert atmosphere 2.2: 1 h / 20 °C / |Inert atmosphere 3.1: caesium carbonate / water; toluene / 0.5 h / |Inert atmosphere; |Sealed tube 3.2: 4 h / 120 °C / |Inert atmosphere; |Sealed tube 4.1: lithium hydroxide hydrate / 1,4-dioxane; methanol; water / |Heating 5.1: hydrogen; palladium 10 on activated carbon / methanol; ethyl acetate / 12 h / 20 °C / |Inert atmosphere View Scheme

potassium hydroxide; iodine in N,N-dimethyl-formamide T=23°C; 4 h;

hydrazine hydrate Reflux;