pyridinium hydrobromide perbromide in ethanol 65 h; Ambient temperature;

1.1: 82 percent / pyridinium chlorochromate / CH2Cl2 / 20 °C 2.1: Sudan III; O3 / CH2Cl2 / -78 °C 2.2: 79 percent / PPh3 / CH2Cl2 / -78 - 20 °C 3.1: 81 percent / ammonium acetate / ethanol / 80 °C 4.1: 80 percent / liquid ammonia; Na / tetrahydrofuran / -78 °C 5.1: 52 percent / pyridinium tribromide / ethanol / 55 h / 20 °C View Scheme

1.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating 1.2: 96 percent / tetrahydrofuran / -78 °C 2.1: 82 percent / pyridinium chlorochromate / CH2Cl2 / 20 °C 3.1: Sudan III; O3 / CH2Cl2 / -78 °C 3.2: 79 percent / PPh3 / CH2Cl2 / -78 - 20 °C 4.1: 81 percent / ammonium acetate / ethanol / 80 °C 5.1: 80 percent / liquid ammonia; Na / tetrahydrofuran / -78 °C 6.1: 52 percent / pyridinium tribromide / ethanol / 55 h / 20 °C View Scheme

1: thionyl chloride / 1 h / Heating 2: 1.) Mg 3: 56 percent / CH3CO2NH4 / acetic acid / Heating 4: 99 percent / pyridinium hydrobromide perbromide / ethanol / 0.17 h / Ambient temperature 5: 86 percent / 1M BBr3 / CH2Cl2 / 12 h / -20 °C View Scheme

1: 96 percent / KOH / methanol; H2O / 4 h / Heating 2: thionyl chloride / 1 h / Heating 3: 1.) Mg 4: 56 percent / CH3CO2NH4 / acetic acid / Heating 5: 99 percent / pyridinium hydrobromide perbromide / ethanol / 0.17 h / Ambient temperature 6: 86 percent / 1M BBr3 / CH2Cl2 / 12 h / -20 °C View Scheme

1: 1.) Mg 2: 56 percent / CH3CO2NH4 / acetic acid / Heating 3: 99 percent / pyridinium hydrobromide perbromide / ethanol / 0.17 h / Ambient temperature 4: 86 percent / 1M BBr3 / CH2Cl2 / 12 h / -20 °C View Scheme

1: 1.) Mg / 1.) THF, room temperature, 1 h; 2.) THF, room temperature, 48 h 2: 61 percent / pyridinium dichromate / dimethylformamide / 9 h / Ambient temperature 3: 56 percent / CH3CO2NH4 / acetic acid / Heating 4: 99 percent / pyridinium hydrobromide perbromide / ethanol / 0.17 h / Ambient temperature 5: 86 percent / 1M BBr3 / CH2Cl2 / 12 h / -20 °C View Scheme

1: 56 percent / CH3CO2NH4 / acetic acid / Heating 2: 99 percent / pyridinium hydrobromide perbromide / ethanol / 0.17 h / Ambient temperature 3: 86 percent / 1M BBr3 / CH2Cl2 / 12 h / -20 °C View Scheme

1: 61 percent / pyridinium dichromate / dimethylformamide / 9 h / Ambient temperature 2: 56 percent / CH3CO2NH4 / acetic acid / Heating 3: 99 percent / pyridinium hydrobromide perbromide / ethanol / 0.17 h / Ambient temperature 4: 86 percent / 1M BBr3 / CH2Cl2 / 12 h / -20 °C View Scheme

1: 99 percent / pyridinium hydrobromide perbromide / ethanol / 0.17 h / Ambient temperature 2: 86 percent / 1M BBr3 / CH2Cl2 / 12 h / -20 °C View Scheme