sodium hydride in dichloromethane; N,N-dimethyl-formamide Ambient temperature;

1: NBS, benzoylperoxide / CCl4 / 5 h / Heating 2: 35 percent / 0.2 N NaOH / methanol / 20 °C 3: 95 percent / H2 / PtO2, 80percent / methanol / 20 h / 25 °C / 735.5 Torr 4: 64 percent / 2,6-lutidine / benzene 5: 78 percent / NaH / dimethylformamide; CH2Cl2 / Ambient temperature View Scheme

1: 35 percent / 0.2 N NaOH / methanol / 20 °C 2: 95 percent / H2 / PtO2, 80percent / methanol / 20 h / 25 °C / 735.5 Torr 3: 64 percent / 2,6-lutidine / benzene 4: 78 percent / NaH / dimethylformamide; CH2Cl2 / Ambient temperature View Scheme

1: 95 percent / H2 / PtO2, 80percent / methanol / 20 h / 25 °C / 735.5 Torr 2: 64 percent / 2,6-lutidine / benzene 3: 78 percent / NaH / dimethylformamide; CH2Cl2 / Ambient temperature View Scheme

1: 64 percent / 2,6-lutidine / benzene 2: 78 percent / NaH / dimethylformamide; CH2Cl2 / Ambient temperature View Scheme

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

1: 90 percent / water, NaOH / pyridine; methanol / 24 h / Heating 2: 48 percent / BBr3 / CH2Cl2 / 24 h / -35 °C View Scheme