sodium hydroxide in methanol T=20°C;

1: NBS, benzoylperoxide / CCl4 / 5 h / Heating; Irradiation 2: 32 percent / 0.2 N NaOH / methanol / 20 °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

copper acetylacetonate; sodium tetrahydroborate in ethanol; isopropyl alcohol T=30°C; 1 h;