1.1: 75 percent / Br2; Fe; NaOAc / acetic acid / 1 h / 20 °C 2.1: [(ν3-C3H5)PdCl]2; (1S,2S)-bis(N,N'-(o-(PPh2)C6H4CO)-1,2-diphenylethylamine; Et3N / CH2Cl2 / 8 h / 20 °C 3.1: TsOH*H2O / methanol / 4 h / 50 °C 4.1: DIBAlH / toluene; hexane / 1.5 h / -78 °C 5.1: Ph3P; diisopropylazodicarboxylate / diethyl ether / 0.33 h / -20 °C 5.2: diethyl ether / 12 h / -20 - 20 °C 5.3: 1.34 g / aq. TsOH / tetrahydrofuran / 4 h / 20 °C 6.1: 91 percent / Pd(OAc)2; Ag2CO3; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 24 h / 107 °C 7.1: 91 percent / PPh3 / CH2Cl2 / 0.17 h / 0 °C 8.1: 88 percent / Pd(PPh3)4; Bu3SnH / toluene / 0.33 h 9.1: 65 percent / Pd(OAc)2; Ag2CO3; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 4 h / 107 °C 10.1: SeO2; quartz sand / dioxane / 1.33 h / 75 °C 11.1: DIBALH / CH2Cl2; hexane; diethyl ether / -78 - 0 °C 11.2: NH4Br / various solvents / 2 h / 20 °C 11.3: 89 percent / NaBH4 / various solvents / 20 °C 12.1: LDA / tetrahydrofuran; hexane / -78 - 20 °C 12.2: 57 percent / tetrahydrofuran; hexane / 6 h / 20 °C / Irradiation View Scheme

1: 90 percent / Cl2 2: 66 percent / K2CO3 / dimethylformamide / 0.08 h / Heating View Scheme

in N-methyl-acetamide; tetrachloromethane; ethanol; acetonitrile

1: 90 percent / Cl2 2: 66 percent / K2CO3 / dimethylformamide / 0.08 h / Heating 3: 100 percent / NaBH4 / aq. ethanol / 1 h / 25 °C 4: 97 percent / 12N aq. HCl 5: 96 percent / dimethylsulfoxide / 1.25 h 6: 74 percent / borane / tetrahydrofuran / 1.5 h / Heating 7: 19 percent / 2.5 h / Heating 8: 69 percent / TFA, 36 N H2SO4 / 3.5 h / 25 °C 9: 95 percent / BBr3 / CH2Cl2 / 3 h / 25 °C View Scheme

potassium carbonate; copper(II) oxide in pyridine Ullmann coupling reaction; Heating; Title compound not separated from byproducts;

1: 70 percent / Br2 / acetic acid / 1.5 h / 20 - 25 °C 2: 96 percent / KOH / H2O / 15 h / 50 °C 4: 94 percent / NaBH4 / ethanol / 1.)2 h, 0-5 deg C, 2.) 12 h, 25 deg C View Scheme

perchloric acid; dihydrogen peroxide; vanadium pentoxide 6 h;

3: aqueous alkaline solution 4: aqueous KOH-solution 5: sulfuric acid View Scheme

potassium carbonate in methanol 4 h; Reflux;

potassium carbonate; sodium iodide in ethanol 4.5 h; Heating;