1: nitric acid; acetic acid / 18 h / 10 - 20 °C 2: zinc; ammonium chloride / ethanol; water / 5 h / Reflux View Scheme

nitric acid in acetic acid

1: 69 percent / Br2 / CHCl3; CCl4 / 1) 5 deg C, 20 min, 2) 5 deg C -> 40 deg C, 2 h 2: 95 percent / K2CO3 / dimethylformamide / 2 h / 25 °C 3: 1) K2CO3, 2) 1 M NaOH / 1) DMSO, 25 deg C, 10 min, 2) DMSO, H2O, 25 deg C, 1 h 4: 78 percent / NaBH4 / ethanol / 3 h / 5 - 25 °C 5: 30 percent Chromat. / O2, Rose Bengal / acetonitrile / 13 °C / Irradiation 6: 96 percent / K2CO3 / dimethylformamide / 2 h / 25 °C View Scheme

1: potassium hydroxide / methanol; water / 24.5 h / 0 - 20 °C 2: palladium 10 on activated carbon; hydrogen / methanol; ethyl acetate / 72 h / 20 °C View Scheme

1: 69 percent / Br2 / CHCl3; CCl4 / 1) 5 deg C, 20 min, 2) 5 deg C -> 40 deg C, 2 h 2: 95 percent / K2CO3 / dimethylformamide / 2 h / 25 °C 3: 1) K2CO3, 2) 1 M NaOH / 1) DMSO, 25 deg C, 10 min, 2) DMSO, H2O, 25 deg C, 1 h 4: 78 percent / NaBH4 / ethanol / 3 h / 5 - 25 °C 5: 30 percent Chromat. / O2, Rose Bengal / acetonitrile / 13 °C / Irradiation 6: 96 percent / K2CO3 / dimethylformamide / 2 h / 25 °C 7: 52 percent / CuBr2 / ethyl acetate 8: 92 percent / K2CO3 / dimethylformamide / 2 h / 25 °C 9: 90 percent / K2CO3 / dimethylsulfoxide / 0.17 h / 25 °C 10: O2, Rose Bengal / acetonitrile / 13 °C / Irradiation View Scheme