bromine in acetic acid T=0 - 20°C; 2 h;

1: NaOH / H2O / 4 h / Heating 2: Br2 / CHCl3 / 2 h / 20 °C View Scheme

1: AlCl3 / nitrobenzene / 24 h / 30 °C 2: NaOH / H2O / 4 h / Heating 3: Br2 / CHCl3 / 2 h / 20 °C View Scheme

1: potassium carbonate / acetone / 60 °C 2: bromine / acetic acid / 3 h / 0 - 20 °C View Scheme

1.1: 51 percent / Et3N / dimethylformamide / Heating 2.1: sodium hydride / dimethylformamide / 0.33 h / 0 °C 2.2: 59 percent / dimethylformamide / 18 h / 20 °C View Scheme

triethylamine in N,N-dimethyl-formamide T=120 - 150°C; Bischler indole synthesis; 4 h; Inert atmosphere;

1.1: 51 percent / Et3N / dimethylformamide / Heating 2.1: sodium hydride / dimethylformamide / 0.33 h / 0 °C 2.2: 59 percent / dimethylformamide / 18 h / 20 °C 3.1: 78 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C 4.1: 87 percent / CBr4; Ph3P / tetrahydrofuran / 3 h / 20 °C 5.1: tetrahydrofuran 6.1: H2 / Pd/C / ethanol; tetrahydrofuran / 20 °C View Scheme

in ethanol Heating;

1.1: 51 percent / Et3N / dimethylformamide / Heating 2.1: sodium hydride / dimethylformamide / 0.33 h / 0 °C 2.2: 59 percent / dimethylformamide / 18 h / 20 °C 3.1: 78 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C 4.1: 87 percent / CBr4; Ph3P / tetrahydrofuran / 3 h / 20 °C 5.1: tetrahydrofuran View Scheme

in ethanol 4 h; Heating;