4-(N,N-dimethlyamino)pyridine; methanesulfonyl chloride; lithium chloride in N,N-dimethyl-formamide 6 h; Ambient temperature;

lithium chloride in water; N,N-dimethyl-formamide

1: 80 percent / 1 N aq. NaOH, 10percent aq. hydrogen peroxide / ethanol / 0.33 h / 40 °C 2: 73 percent / conc. sulfuric acid, aq. sodium nitrite / 70 °C 3: 75 percent / conc. sulfuric acid / Heating 4: 66 percent / NO2BF4 / acetonitrile 5: 73 percent / ethanol / 1 h / -78 deg C to room temperature 6: 88 percent / H2 / 5percent Pd/C / methanol / 4 h / 2585.7 Torr 7: 78 percent / pyridine / dimethylformamide / 4 h / Ambient temperature 8: 67 percent / conc. sulfuric acid / acetic acid / 5 h / 100 °C 9: 72 percent / BBr3 / benzene / 7 h / Heating 10: 85 percent / LiCl, (dimethylamino)pyridine, methanesulfonyl chloride / dimethylformamide / 6 h / Ambient temperature View Scheme

1: 71 percent / acetic anhydride, 90percent nitric acid / 0.25 h / Ambient temperature 2: 80 percent / 1 N aq. NaOH, 10percent aq. hydrogen peroxide / ethanol / 0.33 h / 40 °C 3: 73 percent / conc. sulfuric acid, aq. sodium nitrite / 70 °C 4: 75 percent / conc. sulfuric acid / Heating 5: 66 percent / NO2BF4 / acetonitrile 6: 73 percent / ethanol / 1 h / -78 deg C to room temperature 7: 88 percent / H2 / 5percent Pd/C / methanol / 4 h / 2585.7 Torr 8: 78 percent / pyridine / dimethylformamide / 4 h / Ambient temperature 9: 67 percent / conc. sulfuric acid / acetic acid / 5 h / 100 °C 10: 72 percent / BBr3 / benzene / 7 h / Heating 11: 85 percent / LiCl, (dimethylamino)pyridine, methanesulfonyl chloride / dimethylformamide / 6 h / Ambient temperature View Scheme

1: 75 percent / conc. sulfuric acid / Heating 2: 66 percent / NO2BF4 / acetonitrile 3: 73 percent / ethanol / 1 h / -78 deg C to room temperature 4: 88 percent / H2 / 5percent Pd/C / methanol / 4 h / 2585.7 Torr 5: 78 percent / pyridine / dimethylformamide / 4 h / Ambient temperature 6: 67 percent / conc. sulfuric acid / acetic acid / 5 h / 100 °C 7: 72 percent / BBr3 / benzene / 7 h / Heating 8: 85 percent / LiCl, (dimethylamino)pyridine, methanesulfonyl chloride / dimethylformamide / 6 h / Ambient temperature View Scheme

1: 66 percent / NO2BF4 / acetonitrile 2: 73 percent / ethanol / 1 h / -78 deg C to room temperature 3: 88 percent / H2 / 5percent Pd/C / methanol / 4 h / 2585.7 Torr 4: 78 percent / pyridine / dimethylformamide / 4 h / Ambient temperature 5: 67 percent / conc. sulfuric acid / acetic acid / 5 h / 100 °C 6: 72 percent / BBr3 / benzene / 7 h / Heating 7: 85 percent / LiCl, (dimethylamino)pyridine, methanesulfonyl chloride / dimethylformamide / 6 h / Ambient temperature View Scheme

1: 88 percent / H2 / 5percent Pd/C / methanol / 4 h / 2585.7 Torr 2: 78 percent / pyridine / dimethylformamide / 4 h / Ambient temperature 3: 67 percent / conc. sulfuric acid / acetic acid / 5 h / 100 °C 4: 72 percent / BBr3 / benzene / 7 h / Heating 5: 85 percent / LiCl, (dimethylamino)pyridine, methanesulfonyl chloride / dimethylformamide / 6 h / Ambient temperature View Scheme

1: 73 percent / ethanol / 1 h / -78 deg C to room temperature 2: 88 percent / H2 / 5percent Pd/C / methanol / 4 h / 2585.7 Torr 3: 78 percent / pyridine / dimethylformamide / 4 h / Ambient temperature 4: 67 percent / conc. sulfuric acid / acetic acid / 5 h / 100 °C 5: 72 percent / BBr3 / benzene / 7 h / Heating 6: 85 percent / LiCl, (dimethylamino)pyridine, methanesulfonyl chloride / dimethylformamide / 6 h / Ambient temperature View Scheme

1: 72 percent / BBr3 / benzene / 7 h / Heating 2: 85 percent / LiCl, (dimethylamino)pyridine, methanesulfonyl chloride / dimethylformamide / 6 h / Ambient temperature View Scheme

1: 67 percent / conc. sulfuric acid / acetic acid / 5 h / 100 °C 2: 72 percent / BBr3 / benzene / 7 h / Heating 3: 85 percent / LiCl, (dimethylamino)pyridine, methanesulfonyl chloride / dimethylformamide / 6 h / Ambient temperature View Scheme