1: 55 percent / dimethylformamide / 2 h / Heating 2: NaOH, water / methanol / 84 h / Heating View Scheme

1: 1.) Br2, 2.) silver trifluoroacetate in benzene / 1.) CCl4, a) irrad., reflux, 5.75 h, b) reflux, 1.5 h, 2.) CCl4, benzene, 2.5 h 2: lithium methoxide / dimethylformamide / 14 h / 90 °C 3: 92 percent / conc. HCl, H2 / 10 percent Pd/C / acetic acid 4: 98 percent / Br2 / CH2Cl2 5: 68 percent / copper bronze / 2 h / 210 °C 6: 96 percent / LiAlH4 / diethyl ether / 1 h / Heating 7: 88 percent / pyridinium chlorochromate / CH2Cl2 / 0.5 h / Ambient temperature 8: 96 percent / butyllithium / hexane; tetrahydrofuran / 0.5 h / Ambient temperature 9: 92 percent / hexamethylphosphoric acid triamide / 2 h / 160 °C View Scheme

potassium carbonate in acetone 1.5 h; Heating;

1: 85 percent / bromine / CCl4 / -5 °C 2: 92 percent / NBS; AIBN / CCl4 / 4 h / Heating 3: 95 percent / aq. calcium carbonate / dioxane / 10 h / Heating 4: 85 percent / aq. KMnO4 / acetone / 0.5 h / Heating 5: thionyl chloride / 3 h / Heating 6: 8.8 g / pyridine / 2 h / 20 °C View Scheme

1: 92 percent / NBS; AIBN / CCl4 / 4 h / Heating 2: 95 percent / aq. calcium carbonate / dioxane / 10 h / Heating 3: 85 percent / aq. KMnO4 / acetone / 0.5 h / Heating 4: thionyl chloride / 3 h / Heating 5: 8.8 g / pyridine / 2 h / 20 °C View Scheme

1: 85 percent / aq. KMnO4 / acetone / 0.5 h / Heating 2: thionyl chloride / 3 h / Heating 3: 8.8 g / pyridine / 2 h / 20 °C View Scheme

1: 84 percent / KOH / methanol / 1 h / Heating 2: 85 percent / bromine / CCl4 / -5 °C 3: 92 percent / NBS; AIBN / CCl4 / 4 h / Heating 4: 95 percent / aq. calcium carbonate / dioxane / 10 h / Heating 5: 85 percent / aq. KMnO4 / acetone / 0.5 h / Heating 6: thionyl chloride / 3 h / Heating 7: 8.8 g / pyridine / 2 h / 20 °C View Scheme

pyridine T=20°C; 2 h;

1: 54 percent / Br2 / CCl4; CH2Cl2 / 0.08 h / Ambient temperature 2: 98 percent / K2CO3 / acetone / 1.5 h / Heating View Scheme

in N,N-dimethyl-formamide 2 h; Heating;