bromine; acetic acid 1.5 h; Heating / reflux;

1.1: Na; EtOH / benzene / 2 h / 0 °C 1.2: 58 percent / benzene / 3 h / 50 °C 2.1: 66 percent / aq. HCl / ethanol / Heating 3.1: Br2; AcOH / 1.5 h / Heating View Scheme

1: hydrogenchloride / ethanol; water / Reflux 2: bromine; acetic acid / 1.5 h / Reflux View Scheme

1: 66 percent / aq. HCl / ethanol / Heating 2: Br2; AcOH / 1.5 h / Heating View Scheme

1.1: hydrogenchloride / ethanol; water / 2 h / 30 °C / Reflux 2.1: bromine; acetic acid / 15 h / 20 - 110 °C 2.2: 2 h / pH 4 View Scheme

1.1: trichlorophosphate / 2 h / 117 °C / Cooling with ice 2.1: sodium hydroxide; water / tetrahydrofuran / 1.5 h 2.2: 1 h / pH 1.5 - 4 3.1: oxalyl dichloride / N,N-dimethyl-formamide / tetrahydrofuran / 3 h / 20 °C View Scheme

1: With trichlorophosphate in N,N-dimethyl-aniline 1.5 h; Heating / reflux; 2: With sodium hydroxide; water T=0°C;

1: POCl3; N,N-dimethylaniline / 1.5 h / Heating 2: ethanolic NH3 / 1 h / 100 °C View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine; trichlorophosphate / 1.5 h / Reflux 1.2: pH 7 2.1: potassium carbonate / N,N-dimethyl-formamide / 120 °C 3.1: caesium carbonate / copper(l) iodide / ethyl orthosilicate / 14 h / 140 °C 4.1: water / ethanol / 0.5 h / 60 °C 5.1: N-ethyl-N,N-diisopropylamine; HATU / tetrahydrofuran / 20 °C 6.1: sodium hydroxide / dichloromethane; methanol / 0.17 h / 0 °C 6.2: 0.33 h / 0 - 20 °C View Scheme

1.1: trichlorophosphate / 2 h / 117 °C / Cooling with ice 2.1: sodium hydroxide; water / tetrahydrofuran / 1.5 h 2.2: 1 h / pH 1.5 - 4 3.1: oxalyl dichloride / N,N-dimethyl-formamide / tetrahydrofuran / 3 h / 20 °C 4.1: ammonia / 1,4-dioxane / 0.75 h / 20 °C 5.1: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 1.08 h / 0 - 20 °C View Scheme