in acetonitrile 20 h; Heating;

1: 86 percent / HBr / 1 h / 100 - 110 °C 2: 1.) NaOEt / 1.) EtOH, 80 deg C, 10 min, 2.) EtOH, N,N-dimethylacetamide, from 80 deg C to 90 deg C, 5 h 3: aq. KOH / methanol / 8 h / 40 °C 4: 3 h / 150 - 170 °C View Scheme

1: 85 percent / hydrochloric acid / H2O; CH2Cl2 / 20 °C 2: 82 percent / N,N-dimethyl-acetamide / -5 - 20 °C View Scheme

1: 86 percent / HBr / 1 h / 100 - 110 °C 2: 1.) LiNH2 / 1.) liq. NH3, from -50 deg C to -40 deg C, 0.5 h, 2.) THF, liq. NH3, a) -33 deg C, 1 h, b) RT, 4 h 3: NaI / dimethylsulfoxide / 1.5 h / 100 - 125 °C 4: 10percent aq. NaOH / 5 h / 90 - 100 °C View Scheme

1: 86 percent / HBr / 1 h / 100 - 110 °C 2: 1.) NaOEt / 1.) EtOH, 80 deg C, 10 min, 2.) EtOH, N,N-dimethylacetamide, from 80 deg C to 90 deg C, 5 h 3: aq. KOH / methanol / 8 h / 40 °C 4: 3 h / 150 - 170 °C 5: 91 percent / NaI / acetone / 12 h / Heating View Scheme

potassium fluoride; diethylene glycol T=120°C;

hydrogenchloride in dichloromethane; water T=20°C;

1: 50.8 g / toluene-4-sulphonic acid / 16 h / 0 °C 2: 1.) Li 3: 91 percent / BBr3 / CH2Cl2 / 1.) -80 deg C, 3 d, 2.) 72 h 4: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 5: p-TsOH / ethanol / 3 h / Heating 6: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 7: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 8: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme