bromine; potassium bromide in water; acetic acid T=20°C; 1 h;

hydrogenchloride; CH3CO2Na; bromine in acetic acid; ethyl acetate

1: nitric acid / acetic acid / 1 h / 20 °C 2: bromine; potassium bromide / water; acetic acid / 1 h / 20 °C View Scheme

1: 72 percent / K2CO3 / acetone / 5 h / Heating 2: Fe; AcOH / H2O / 1.5 h / Heating 3: 6.60 g / Na2CO3 / dimethylformamide / 25 h / Heating 4: 54 percent / n-BuLi / diethyl ether; hexane / 1.5 h / -78 °C 5: 100 percent / NaH / dimethylformamide / 0 - 20 °C 6: 97 percent / N,N-dimethylbarbituric acid; Pd(PPh3)4 / CH2Cl2 / 2.5 h / Heating 7: 75 percent / Et3N; N,N-dimethylaminopyridine / tetrahydrofuran / 6 h / Heating 8: TBAF / tetrahydrofuran / 24 h / 20 °C 9: 89 percent / diisopropylethylamine / CH2Cl2 / 6 h / -78 °C 10: 72 percent / second generation Grubbs catalyst / toluene / 2 h / Heating 11: DIBAL-H / diethyl ether; hexane / 2 h / -78 °C 12: 52.9 mg / toluene / 3.5 h / Heating 13: TFA / CH2Cl2 / 1.17 h / 0 - 20 °C 14: LiOH; H2O / methanol; tetrahydrofuran / 60 h / 20 °C 15: 6.4 mg / DIPEA; BOPCl / toluene / 37 h / 85 °C 16: CH2Cl2 / 0.67 h / 20 °C 17: K2CO3; MeOH / 1.5 h / 20 °C 18: 2.9 mg / aq. cerium ammonium nitrate / acetonitrile / 1 h / -10 °C View Scheme

1: 96 percent / H2 / tetrahydrofuran / 2.5 h / 1292.87 Torr 2: 46.5 g / pyridine / CH2Cl2 / 0 °C 3: 81 percent / p-toluenesulfonic acid monohydrate; p-xylene / 3 h / Heating 4: 93 percent / BBr3 / CH2Cl2 / -78 - 20 °C 5: 72 percent / dichlorobis(tri-o-tolylphosphine)palladium (II) / 1,2-diethoxy-ethane / 48 h / 115 °C View Scheme

hydrogen in tetrahydrofuran P=1292.87 Torr; 2.5 h;

potassium carbonate in acetone 1.5 h; Heating;

potassium hydroxide in acetone Reflux;