1: 1.) n-BuLi/N-isopropylcyclohexylamine / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 2 h 2: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 3: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min 4: KOH / ethanol / 1 h / Heating 5: 84 percent / HF (g) View Scheme

1: 1.) n-BuLi/N-isopropylcyclohexylamine / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 2 h 2: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 3: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min 4: KOH / ethanol / 1 h / Heating View Scheme

1: 1.) n-BuLi/N-isopropylcyclohexylamine / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 2 h 2: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 3: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min 4: KOH / ethanol / 1 h / Heating 5: 84 percent / HF (g) 6: 96 percent / sodium borohydride / ethanol / 1.83 h / 55 - 60 °C 7: 93 percent / glacial acetic acid, conc. HCl / 0.25 h 8: 60 percent / 10percent palladium on charcoal / 300 - 305 °C View Scheme

1: 1.) n-BuLi/N-isopropylcyclohexylamine / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 2 h 2: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 3: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min 4: KOH / ethanol / 1 h / Heating 5: 84 percent / HF (g) 6: 96 percent / sodium borohydride / ethanol / 1.83 h / 55 - 60 °C View Scheme

1: 1.) n-BuLi/N-isopropylcyclohexylamine / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 2 h 2: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 3: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min 4: KOH / ethanol / 1 h / Heating 5: 84 percent / HF (g) 6: 96 percent / sodium borohydride / ethanol / 1.83 h / 55 - 60 °C 7: 93 percent / glacial acetic acid, conc. HCl / 0.25 h View Scheme

1: 1.) n-BuLi/N-isopropylcyclohexylamine / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 2 h 2: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 3: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min View Scheme