diethyl ether

potassium carbonate

hydrogenchloride

1: NaH / dimethylformamide 2: 1.) LDA / 1.) THF, -78 deg, 10 min 3: DDQ / dioxane / 0.17 h / 60 °C 4: K2CO3 / dimethylsulfoxide / 16 h / 20 °C 5: LAH / tetrahydrofuran / 1 h / 0 °C 6: pyridine / 24 h 7: imidazole / dimethylformamide / 16 h / 0 - 20 °C 8: TsOH / CH2Cl2; methanol / 0.08 h 9: 62 percent / PCC / CH2Cl2 / 20 °C 10: 91 percent / NBS / CH2Cl2 / 0.5 h / 20 °C 11: MCPBA, Na2SO4, 4,4'-methylenebis(2,6-di-t-butyl)phenol / benzene / 1 h / 20 °C 12: aq. NaOH / methanol; tetrahydrofuran / 20 °C 13: K2CO3 / dimethylsulfoxide / 16 h / 20 °C 14: TBAF 15: DEAD, PPh3 16: NaOH 18: 1.) t-BuLi, 2.) FeCl3 / 1.) THF, -78 deg, 2.) -78 deg to 20 deg 19: 1.) TBAF, 2.) H2 / 2.) Pd/C / 1.) THF, 2.) THF, MeOH 20: 65 percent / K3Fe(CN)6, NaOH / H2O; ethanol; tetrahydrofuran / 20 °C 21: 54 percent / DMAP, pyridine 22: aq. HCl View Scheme

1: CCl4; bromine 2: aqueous dioxane View Scheme

1: 90 percent / SO2Cl2 / diethyl ether / 17 h / Ambient temperature 2: 6 percent / diphenyl ether / 5 h / Heating 3: 65 percent / BBr3 / CH2Cl2 / 24 h / Ambient temperature View Scheme

Multistep reaction;

1: 1.) sodium hydride / 1.) benzene, 80 deg C, 1 h, 2.) benzene, a) 35 deg C, b) 45 to 50 deg C, 1 h 2: 68 percent / piperidine / toluene / 5 h / Heating 3: 95 percent / 0.2 N HCl / dioxane / 6 h / 80 °C View Scheme