boron tribromide in hexane; dichloromethane 1.) -70 deg C, 1 h, 2.) RT, 2 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: 37 percent / 2.5 h / Heating 8: TFA, 36 N aq. H2SO4 / 3.5 h / 25 °C 9: BBr3 / CH2Cl2 / 3 h / 25 °C View Scheme

1: TFA, 36 N aq. H2SO4 / 3.5 h / 25 °C 2: 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: 37 percent / 2.5 h / Heating 4: TFA, 36 N aq. H2SO4 / 3.5 h / 25 °C 5: 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: 37 percent / 2.5 h / Heating 6: TFA, 36 N aq. H2SO4 / 3.5 h / 25 °C 7: 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: 37 percent / 2.5 h / Heating 7: TFA, 36 N aq. H2SO4 / 3.5 h / 25 °C 8: BBr3 / CH2Cl2 / 3 h / 25 °C View Scheme

1: 37 percent / 2.5 h / Heating 2: TFA, 36 N aq. H2SO4 / 3.5 h / 25 °C 3: BBr3 / CH2Cl2 / 3 h / 25 °C View Scheme

1: 74 percent / borane / tetrahydrofuran / 1.5 h / Heating 2: 37 percent / 2.5 h / Heating 3: TFA, 36 N aq. H2SO4 / 3.5 h / 25 °C 4: 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: 37 percent / 2.5 h / Heating 5: TFA, 36 N aq. H2SO4 / 3.5 h / 25 °C 6: BBr3 / CH2Cl2 / 3 h / 25 °C View Scheme

1: 95 percent / trifluoroacetic acid, H2SO4 / 3 h / Heating 2: 69 percent / glacial acetic acid, bromine / 2 h / Ambient temperature 3: 85 percent / formic acid / 4 h / Heating 4: 1.) n-BuLi, 2.) hexachloroethane / 1.) Et2O, THF, -70 deg C, 10 min, 2.) Et2O, THF, -70 deg C, 5 min 5: 3.1 g / benzene / 3 h / 60 °C 6: aq. HCl / acetic acid / 100 °C 7: 90 percent / boron tribromide / CH2Cl2; hexane / 1.) -70 deg C, 1 h, 2.) RT, 2 h View Scheme