potassium hydroxide in methanol; water

phosphoric acid; acetic acid

hydrogenchloride in water

PPA; water T=90°C; 1.33 h;

1: lithium aluminum hydride / tetrahydrofuran / 1 h 2: dimethylformamide; H2O / 0.33 h / Ambient temperature 3: 78.4 percent / sodium hydroxide; HCl / methanol; H2O / 1 h / Heating 4: 92 percent / dry hydrogen bromide / tetrahydrothiophene 1,1-dioxide / 3 h / 15 °C 5: sodium hydroxide / methanol; H2O / 1 h / Heating 6: 90 percent / 85percent phosphoric acid / acetic acid / 7 h / Heating 7: 75.1 percent / polyphosphoric acid, water / 1.33 h / 90 °C View Scheme

1: 85.6 percent / chlorosulfonic acid / 2 h / 120 - 125 °C 2: lithium aluminum hydride / tetrahydrofuran / 1 h 3: dimethylformamide; H2O / 0.33 h / Ambient temperature 4: 78.4 percent / sodium hydroxide; HCl / methanol; H2O / 1 h / Heating 5: 92 percent / dry hydrogen bromide / tetrahydrothiophene 1,1-dioxide / 3 h / 15 °C 6: sodium hydroxide / methanol; H2O / 1 h / Heating 7: 90 percent / 85percent phosphoric acid / acetic acid / 7 h / Heating 8: 75.1 percent / polyphosphoric acid, water / 1.33 h / 90 °C View Scheme

1: dimethylformamide; H2O / 0.33 h / Ambient temperature 2: 78.4 percent / sodium hydroxide; HCl / methanol; H2O / 1 h / Heating 3: 92 percent / dry hydrogen bromide / tetrahydrothiophene 1,1-dioxide / 3 h / 15 °C 4: sodium hydroxide / methanol; H2O / 1 h / Heating 5: 90 percent / 85percent phosphoric acid / acetic acid / 7 h / Heating 6: 75.1 percent / polyphosphoric acid, water / 1.33 h / 90 °C View Scheme

1: 1.) bromine, 2.) potassium carbonate / 1.) dichloromethane, irradiated, 2.75 h, 2.) water, 5-12 deg C, 30 min; 12 deg C, 40 min. 2: sodium borohydride, boron trifluoride etherate / tetrahydrofuran / 5 h / 10 - 15 °C 3: 78.4 percent / sodium hydroxide; HCl / methanol; H2O / 1 h / Heating 4: 92 percent / dry hydrogen bromide / tetrahydrothiophene 1,1-dioxide / 3 h / 15 °C 5: 95.2 percent / dioxane; H2O / 1 h / 70 °C 6: 90 percent / 85percent phosphoric acid / acetic acid / 7 h / Heating 7: 75.1 percent / polyphosphoric acid, water / 1.33 h / 90 °C View Scheme

1: 92 percent / dry hydrogen bromide / tetrahydrothiophene 1,1-dioxide / 3 h / 15 °C 2: dimethylformamide; H2O / 0.33 h / Ambient temperature 3: 93.2 percent / dry hydrogen bromide / tetrahydrothiophene 1,1-dioxide / 2.75 h / 15 °C 4: acetone; H2O / 1 h / Heating 5: 90 percent / conc. sulfuric acid / methanol; H2O / 23 h / Heating 6: 75.1 percent / polyphosphoric acid, water / 1.33 h / 90 °C View Scheme

1: 78.4 percent / sodium hydroxide; HCl / methanol; H2O / 1 h / Heating 2: 92 percent / dry hydrogen bromide / tetrahydrothiophene 1,1-dioxide / 3 h / 15 °C 3: 95.2 percent / dioxane; H2O / 1 h / 70 °C 4: 90 percent / 85percent phosphoric acid / acetic acid / 7 h / Heating 5: 75.1 percent / polyphosphoric acid, water / 1.33 h / 90 °C View Scheme