zinc in dimethyl sulfoxide T=55°C; 4 h; sealed tube, vacuum;

1: 92 percent / PBr3 / CH2Cl2 / 0.5 h 2: 73 percent / Zn-powder / dimethylsulfoxide / 4 h / 55 °C / sealed tube, vacuum View Scheme

1: 74 percent / Aluminum chloride / CH2Cl2 / 0.25 h / -50 - -20 °C 2: 55 percent / Hydrochloric acid / 3.75 h / 55 °C 3: KOH, Bromine / dioxane / 17 h / Ambient temperature 4: 72 percent / Lithium aluminum hydride / tetrahydrofuran / 96 h / Heating 5: Acetic anhydride, p-toluenesulfonic acid / acetic acid / Heating 6: Boron trifluoride-etherate / benzene / 0.5 h / Ambient temperature 7: 1.) tosylhydrazine, sulfuric acid; 2.) sodium methoxide / 1.) Benzene, reflux, 15 min; 2.) THF, irradiation, 20 deg C, 70 min. View Scheme

1: 55 percent / Hydrochloric acid / 3.75 h / 55 °C 2: KOH, Bromine / dioxane / 17 h / Ambient temperature 3: 72 percent / Lithium aluminum hydride / tetrahydrofuran / 96 h / Heating 4: Acetic anhydride, p-toluenesulfonic acid / acetic acid / Heating 5: Boron trifluoride-etherate / benzene / 0.5 h / Ambient temperature 6: 1.) tosylhydrazine, sulfuric acid; 2.) sodium methoxide / 1.) Benzene, reflux, 15 min; 2.) THF, irradiation, 20 deg C, 70 min. View Scheme

1: KOH, Bromine / dioxane / 17 h / Ambient temperature 2: 72 percent / Lithium aluminum hydride / tetrahydrofuran / 96 h / Heating 3: Acetic anhydride, p-toluenesulfonic acid / acetic acid / Heating 4: Boron trifluoride-etherate / benzene / 0.5 h / Ambient temperature 5: 1.) tosylhydrazine, sulfuric acid; 2.) sodium methoxide / 1.) Benzene, reflux, 15 min; 2.) THF, irradiation, 20 deg C, 70 min. View Scheme

1: 72 percent / Lithium aluminum hydride / tetrahydrofuran / 96 h / Heating 2: Acetic anhydride, p-toluenesulfonic acid / acetic acid / Heating 3: Boron trifluoride-etherate / benzene / 0.5 h / Ambient temperature 4: 1.) tosylhydrazine, sulfuric acid; 2.) sodium methoxide / 1.) Benzene, reflux, 15 min; 2.) THF, irradiation, 20 deg C, 70 min. View Scheme

1: 60 percent / AlCl3, HCl / CH2Cl2 / 0.5 h / 0 °C 2: 1.) p-TsNHNH2, HCl, 2.) NaOMe / 1.) THF, reflux, 30 min, 2.) irradiation, 22 h View Scheme

1: 27 percent / LiAlH4 / tetrahydrofuran / 20 h / Heating 2: 60 percent / AlCl3, HCl / CH2Cl2 / 0.5 h / 0 °C 3: 1.) p-TsNHNH2, HCl, 2.) NaOMe / 1.) THF, reflux, 30 min, 2.) irradiation, 22 h View Scheme

sulfuric acid; sodium methylate; toluene-4-sulfonic acid hydrazide 1.) Benzene, reflux, 15 min; 2.) THF, irradiation, 20 deg C, 70 min.; Yield given. Multistep reaction;

1: 91 percent / act. MnO2 / CHCl3 / 66 h / Ambient temperature 2: 1.) p-TsNHNH2, HCl, 2.) NaOMe / 1.) THF, reflux, 30 min, 2.) irradiation, 22 h View Scheme