boron tribromide in dichloromethane T=-30°C; 0.0833333 h;

1: 60 percent / NBS, benzoylperoxide / CCl4 / 5 h / Heating; Irradiation 2: 40 percent / 0.2 N NaOH / methanol / Ambient temperature 3: 90 percent / H2 / PtO2, 80percent / methanol / 20 h / 25 °C / 735.5 Torr 4: 50 percent / 2,6-lutidine / benzene 5: 65 percent / NaH / dimethylformamide; CH2Cl2 / Ambient temperature 6: water, 0.1 N NaOH / pyridine; methanol / 24 h / Heating View Scheme

1: 90 percent / H2 / PtO2, 80percent / methanol / 20 h / 25 °C / 735.5 Torr 2: 50 percent / 2,6-lutidine / benzene 3: 65 percent / NaH / dimethylformamide; CH2Cl2 / Ambient temperature 4: water, 0.1 N NaOH / pyridine; methanol / 24 h / Heating View Scheme

boron tribromide in dichloromethane T=-30°C; 0.0833333 h;

sodium hydroxide; water in pyridine; methanol 24 h; Heating; Yield given;

1: NBS, benzoylperoxide / CCl4 / 5 h / Heating; Irradiation 2: 32 percent / 0.2 N NaOH / methanol / 20 °C 3: 80 percent / NaBH4, Cu(II) acetylacetonate / ethanol; propan-2-ol / 1 h / 30 °C 4: 50 percent / 2,6-lutidine / benzene 5: 80 percent / NaH / dimethylformamide; CH2Cl2 / Ambient temperature 6: BBr3, aq.NaHCO3 / CH2Cl2 / -35 °C View Scheme

1: 50 percent / 2,6-lutidine / benzene 2: 65 percent / NaH / dimethylformamide; CH2Cl2 / Ambient temperature 3: water, 0.1 N NaOH / pyridine; methanol / 24 h / Heating View Scheme

1: 32 percent / 0.2 N NaOH / methanol / 20 °C 2: 80 percent / NaBH4, Cu(II) acetylacetonate / ethanol; propan-2-ol / 1 h / 30 °C 3: 50 percent / 2,6-lutidine / benzene 4: 80 percent / NaH / dimethylformamide; CH2Cl2 / Ambient temperature 5: BBr3, aq.NaHCO3 / CH2Cl2 / -35 °C View Scheme

1: 50 percent / 2,6-lutidine / benzene 2: 80 percent / NaH / dimethylformamide; CH2Cl2 / Ambient temperature 3: BBr3, aq.NaHCO3 / CH2Cl2 / -35 °C View Scheme

1: 80 percent / NaBH4, Cu(II) acetylacetonate / ethanol; propan-2-ol / 1 h / 30 °C 2: 50 percent / 2,6-lutidine / benzene 3: 80 percent / NaH / dimethylformamide; CH2Cl2 / Ambient temperature 4: BBr3, aq.NaHCO3 / CH2Cl2 / -35 °C View Scheme