1: 89 percent / benzene / 24 h / Ambient temperature 2: 98 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -35 deg C, 30 min, 2.) -30 deg C, 3 h 3: 66 percent / conc. hydrochloric acid / 0.08 h / Heating 4: 76.7 percent / sodium borohydride / ethanol / Ambient temperature View Scheme

phosphorus tribromide in diethyl ether 2.5 h; Ambient temperature;

1: sodium tetrahydroborate / dichloromethane / 0.5 h / 20 °C 2: phosphorus tribromide / dichloromethane / 0.5 h / 0 °C View Scheme

1: 89 percent / benzene / 24 h / Ambient temperature 2: 98 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -35 deg C, 30 min, 2.) -30 deg C, 3 h 3: 90 percent / conc. hydrochloric acud / Heating 4: 68 percent / 1.) 10 percent acetic acid, sodium acetate, 2.) NaI / 0.25 h / Heating View Scheme

1: 99 percent / benzene / 5 h / Heating 2: n-BuLi / tetrahydrofuran; hexane / 16 h / Heating 3: H2 / Pd-C / 2-methyl-propan-2-ol View Scheme

1: 99 percent / benzene / 5 h / Heating 2: n-BuLi / tetrahydrofuran; hexane / 16 h / Heating 3: H2 / Pd-C / 2-methyl-propan-2-ol 4: 78 percent / BBr3 / CH2Cl2 5: pyridine / 4 h / Ambient temperature View Scheme

ethanol

1: 89 percent / benzene / 24 h / Ambient temperature 2: 98 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -35 deg C, 30 min, 2.) -30 deg C, 3 h 3: 66 percent / conc. hydrochloric acid / 0.08 h / Heating 4: 76.7 percent / sodium borohydride / ethanol / Ambient temperature 5: 95 percent / iodine, potassium acetate / methanol / Heating View Scheme

1: 99 percent / benzene / 5 h / Heating 2: n-BuLi / tetrahydrofuran; hexane / 16 h / Heating 3: H2 / Pd-C / 2-methyl-propan-2-ol 4: 78 percent / BBr3 / CH2Cl2 View Scheme