1: 68 percent / NaH / 1,2-dimethoxy-ethane / Ambient temperature 2: 75 percent / Na acetamide / 1 h / 120 °C 3: pyridine / 80 °C 4: 74 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 0.5 h / Heating 5: NBS, K2CO3, benzoyl peroxide / CCl4 / 4 h / Heating 6: 1) AgCO3; 2) triethylamine / 1) H2O, dioxane, r.t., 48 h; 2) H2O, dioxane, r.t., 36 h 7: 94 percent / K acetate, Pd/C / H2O; methanol 8: 71 percent / chromic anhydride-pyridine complex / 24 h / 40 °C 9: NH2OH / ethanol 10: 1) acetic anhydride, pyridine; 2) conc. ammonia / 2) CH3OH 11: CF3COOH / 2 h / 60 °C 12: cc. NH3 / dioxane / 2 h / 60 °C View Scheme