bromine; sodium acetate in acetic acid T=80 - 90°C; 2 h;

bromine; sodium acetate in acetic acid T=85°C; 2.5 h;

iron sulphate heptahydrate; sulfuric acid; boric acid; m-nitrobenzene sulfonic acid sodium salt in water T=135°C; Skraup Quinoline Synthesis; 18 h;

1: thionyl chloride / 8 h / |Inert atmosphere; |Reflux 2: ammonia / dichloromethane / 0.33 h / -30 °C 3: sodium hydroxide; bromine / water / 0.92 h / 0 - 80 °C 4: sulfuric acid; iron sulphate heptahydrate; m-nitrobenzene sulfonic acid sodium salt; boric acid / water / 18 h / 135 °C View Scheme

1: ammonia / dichloromethane / 0.33 h / -30 °C 2: sodium hydroxide; bromine / water / 0.92 h / 0 - 80 °C 3: sulfuric acid; iron sulphate heptahydrate; m-nitrobenzene sulfonic acid sodium salt; boric acid / water / 18 h / 135 °C View Scheme

1: caesium carbonate / 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 16 h / Reflux; Inert atmosphere 2: hydrogenchloride; water / methanol / 2 h / 50 °C View Scheme

1.1: caesium carbonate / 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 16 h / Reflux; Inert atmosphere 2.1: hydrogenchloride; water / methanol / 2 h / 50 °C 3.1: hydrogenchloride / water / 0.25 h / 0 - 5 °C 3.2: 1 h / 0 - 5 °C 3.3: 1 h / 60 °C View Scheme

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 18 h / 0 - 20 °C 2: trichlorophosphate / dichloromethane / 18 h / Reflux View Scheme

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 18 h / 0 - 20 °C 2: trichlorophosphate / dichloromethane / 2.5 h / |Reflux View Scheme