lithium hexamethyldisilazane; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl; tris-(dibenzylideneacetone)dipalladium(0) in tetrahydrofuran T=65°C; 20 h;

hydrogenchloride; sodium hydroxide 3 h; Heating;

1: PCl5 / steam bath 2: 49 percent / Na / ethanol; dioxane / 0.5 h / 30 - 35 °C 3: 75 percent / 1 h / 270 °C 4: 34 percent / SeO2 / dioxane; H2O / 18 h / Heating 5: 97 percent / SOCl2, dimethylformamide / benzene / 1 h / Heating 6: 90 percent / NaN3 / acetone; H2O / 0.5 h 7: aq. acetic acid / 0.33 h / 85 - 90 °C 8: 40 percent / aq. HCl; 2.5 N NaOH / 3 h / Heating View Scheme

1: 34 percent / SeO2 / dioxane; H2O / 18 h / Heating 2: 97 percent / SOCl2, dimethylformamide / benzene / 1 h / Heating 3: 90 percent / NaN3 / acetone; H2O / 0.5 h 4: aq. acetic acid / 0.33 h / 85 - 90 °C 5: 40 percent / aq. HCl; 2.5 N NaOH / 3 h / Heating View Scheme

1: 75 percent / 1 h / 270 °C 2: 34 percent / SeO2 / dioxane; H2O / 18 h / Heating 3: 97 percent / SOCl2, dimethylformamide / benzene / 1 h / Heating 4: 90 percent / NaN3 / acetone; H2O / 0.5 h 5: aq. acetic acid / 0.33 h / 85 - 90 °C 6: 40 percent / aq. HCl; 2.5 N NaOH / 3 h / Heating View Scheme

1: 90 percent / NaN3 / acetone; H2O / 0.5 h 2: aq. acetic acid / 0.33 h / 85 - 90 °C 3: 40 percent / aq. HCl; 2.5 N NaOH / 3 h / Heating View Scheme

1: 97 percent / SOCl2, dimethylformamide / benzene / 1 h / Heating 2: 90 percent / NaN3 / acetone; H2O / 0.5 h 3: aq. acetic acid / 0.33 h / 85 - 90 °C 4: 40 percent / aq. HCl; 2.5 N NaOH / 3 h / Heating View Scheme

1: 49 percent / Na / ethanol; dioxane / 0.5 h / 30 - 35 °C 2: 75 percent / 1 h / 270 °C 3: 34 percent / SeO2 / dioxane; H2O / 18 h / Heating 4: 97 percent / SOCl2, dimethylformamide / benzene / 1 h / Heating 5: 90 percent / NaN3 / acetone; H2O / 0.5 h 6: aq. acetic acid / 0.33 h / 85 - 90 °C 7: 40 percent / aq. HCl; 2.5 N NaOH / 3 h / Heating View Scheme