1: 1) 48percent HBr, NaNO2 2) CuBr / 1) water, 1 h, 0 deg C 2) a) 30 min, r.t. b) 90 min, 70 deg C 2: SOCl2 / CH2Cl2 / 1 h / Heating 3: NH3-gas / CH2Cl2 / 1 h 4: 79 percent / Br2, NaOH / 1) 4 h, 0 deg C 2) 3 h, 60 deg C View Scheme

1: NH3-gas / CH2Cl2 / 1 h 2: 79 percent / Br2, NaOH / 1) 4 h, 0 deg C 2) 3 h, 60 deg C View Scheme

1: SOCl2 / CH2Cl2 / 1 h / Heating 2: NH3-gas / CH2Cl2 / 1 h 3: 79 percent / Br2, NaOH / 1) 4 h, 0 deg C 2) 3 h, 60 deg C View Scheme

1.1: sodium hydroxide / ethanol / Reflux 2.1: sodium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere 3.1: sodium hydroxide / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 4.1: hydrogenchloride / ethanol; water / Reflux View Scheme

1: sodium hydroxide / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 2: hydrogenchloride / ethanol; water / Reflux View Scheme

1: t-BuOLi; carbon tetrabromide / N,N-dimethyl-formamide / 4 h / 60 °C / Inert atmosphere 2: hydrogenchloride; iron / ethanol; water / 2 h / Reflux View Scheme

1.1: sodium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 1.2: 2 h / 20 °C / Inert atmosphere 2.1: sodium hydroxide / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 3.1: hydrogenchloride / ethanol; water / Reflux View Scheme

1.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C 2.1: sodium hydroxide / ethanol / Reflux 3.1: sodium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 3.2: 2 h / 20 °C / Inert atmosphere 4.1: sodium hydroxide / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 5.1: hydrogenchloride / ethanol; water / Reflux View Scheme

1: pyridine / dichloromethane; water 2: CuI / Pd(PPh3)2Cl2 / ethyl acetate; triethylamine; Petroleum ether 3: potassium tert-butylate / N,N-dimethyl-formamide 4: KNO3 / sulfuric acid; ethyl acetate; Petroleum ether View Scheme