1: H2O 2: MnO2 / CH2Cl2 View Scheme

1: 56 percent / Br2 / CHCl3 / Ambient temperature 2: 85 percent / Na2SO3 / H2O; ethanol / 18 h / Heating 3: 78 percent / aq. NaOH / ethanol / Ambient temperature 4: 81 percent / MnO2 / CH2Cl2; dioxane / Heating View Scheme

n-butyllithium; sodium methylate in tetrahydrofuran; methanol; hexane; toluene-4-sulfonic acid

sodium methylate in methanol

sodium hydride 1.) DMF, RT, 80 min, 2.) DMF, 2,5 h; Yield given. Multistep reaction;

1: 97 percent / iodine, Na2CO3 / dioxane; H2O / 23 h / Ambient temperature 2: 99 percent / K2CO3 / dimethylformamide / 19 h 3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, 30 min View Scheme

1: 97 percent / iodine, Na2CO3 / dioxane; H2O / 23 h / Ambient temperature 2: 99 percent / K2CO3 / dimethylformamide / 19 h 3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, 30 min 4: 98 percent / conc. HCl / aq. ethanol / 1.25 h / Heating 5: 91 percent / K2CO3 / dimethylformamide / 17 h / 80 °C 6: 96 percent / H2, NaOAc / 10percent Pd/C / methanol / 18 h 7: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, 30 min 8: DMAP / CH2Cl2 / 2 h / Ambient temperature 9: DBU / toluene / 3 h / 80 °C 10: 58 percent / 3.75 M aq. NaOH / aq. ethanol / 4 h View Scheme

1: H2O 2: MnO2 / CH2Cl2 3: N-chlorosuccinimide 4: K2CO3 / dimethylformamide 5: H2 / Pd/C View Scheme

1: 97 percent / iodine, Na2CO3 / dioxane; H2O / 23 h / Ambient temperature 2: 99 percent / K2CO3 / dimethylformamide / 19 h 3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, 30 min 4: 98 percent / conc. HCl / aq. ethanol / 1.25 h / Heating 5: 91 percent / K2CO3 / dimethylformamide / 17 h / 80 °C 6: 96 percent / H2, NaOAc / 10percent Pd/C / methanol / 18 h 7: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, 30 min 8: DMAP / CH2Cl2 / 2 h / Ambient temperature 9: DBU / toluene / 3 h / 80 °C View Scheme

sodium hydride 1.) DMF, RT, 1 h, 2.) DMF, RT, 19 h; Yield given. Multistep reaction;