1: With sulfuric acid; trifluoroacetic acid in dichloromethane T=0°C; 2 h; 2: With ammonia; water in dichloromethane T=20°C; 3: With hydrogen bromide in water T=107°C; 16 h;

boron tribromide in dichloromethane T=25°C; 3 h;

1: 90 percent / Cl2 2: 66 percent / K2CO3 / dimethylformamide / 0.08 h / Heating 3: 100 percent / NaBH4 / aq. ethanol / 1 h / 25 °C 4: 97 percent / 12N aq. HCl 5: 96 percent / dimethylsulfoxide / 1.25 h 6: 74 percent / borane / tetrahydrofuran / 1.5 h / Heating 7: 19 percent / 2.5 h / Heating 8: 69 percent / TFA, 36 N H2SO4 / 3.5 h / 25 °C 9: 95 percent / BBr3 / CH2Cl2 / 3 h / 25 °C View Scheme

1: 96 percent / dimethylsulfoxide / 1.25 h 2: 74 percent / borane / tetrahydrofuran / 1.5 h / Heating 3: 19 percent / 2.5 h / Heating 4: 69 percent / TFA, 36 N H2SO4 / 3.5 h / 25 °C 5: 95 percent / BBr3 / CH2Cl2 / 3 h / 25 °C View Scheme

1: 100 percent / NaBH4 / aq. ethanol / 1 h / 25 °C 2: 97 percent / 12N aq. HCl 3: 96 percent / dimethylsulfoxide / 1.25 h 4: 74 percent / borane / tetrahydrofuran / 1.5 h / Heating 5: 19 percent / 2.5 h / Heating 6: 69 percent / TFA, 36 N H2SO4 / 3.5 h / 25 °C 7: 95 percent / BBr3 / CH2Cl2 / 3 h / 25 °C View Scheme

1: 66 percent / K2CO3 / dimethylformamide / 0.08 h / Heating 2: 100 percent / NaBH4 / aq. ethanol / 1 h / 25 °C 3: 97 percent / 12N aq. HCl 4: 96 percent / dimethylsulfoxide / 1.25 h 5: 74 percent / borane / tetrahydrofuran / 1.5 h / Heating 6: 19 percent / 2.5 h / Heating 7: 69 percent / TFA, 36 N H2SO4 / 3.5 h / 25 °C 8: 95 percent / BBr3 / CH2Cl2 / 3 h / 25 °C View Scheme

1: 19 percent / 2.5 h / Heating 2: 69 percent / TFA, 36 N H2SO4 / 3.5 h / 25 °C 3: 95 percent / BBr3 / CH2Cl2 / 3 h / 25 °C View Scheme

1: 74 percent / borane / tetrahydrofuran / 1.5 h / Heating 2: 19 percent / 2.5 h / Heating 3: 69 percent / TFA, 36 N H2SO4 / 3.5 h / 25 °C 4: 95 percent / BBr3 / CH2Cl2 / 3 h / 25 °C View Scheme

1: 97 percent / 12N aq. HCl 2: 96 percent / dimethylsulfoxide / 1.25 h 3: 74 percent / borane / tetrahydrofuran / 1.5 h / Heating 4: 19 percent / 2.5 h / Heating 5: 69 percent / TFA, 36 N H2SO4 / 3.5 h / 25 °C 6: 95 percent / BBr3 / CH2Cl2 / 3 h / 25 °C View Scheme

1: 86.4 percent / Br2 / CH2Cl2 / -5 - 0 °C 2: 95 percent / MgSO4, MgO / 1.25 h / Heating 3: K2CO3 / dimethylformamide / 2 h / 110 °C 4: 10percent aq. H2SO4 / Heating 5: 69 percent / TFA, 36 N H2SO4 / 3.5 h / 25 °C 6: 95 percent / BBr3 / CH2Cl2 / 3 h / 25 °C View Scheme