1: 94 percent / Adogen 464, potassium nitrosodisulfonate, 1/6 M KH2PO4 / benzene; H2O / 2 h / Ambient temperature 2: 1.) KBH4, 2.) pyridine / 1.) ethanol, 21 h, 2.) 0 deg C, overnight 3: 84 percent / ammonia, methanol / 96 h / Ambient temperature View Scheme

boron tribromide in dichloromethane 1.) -78 deg C, 1 h, 2.) RT, 2 h;

1: 100 percent / methanesulfonic acid / 1.5 h / Ambient temperature 2: 59 percent / zinc amalgam, conc. HCl / toluene; acetic acid / 27 h / Heating 3: 1.) n-BuLi / 1.) ether, hexane, -30 deg C, 1 h, 2.) ether, hexane, from -30 deg C to RT 4: 69 percent / conc,. H2SO4 / benzene / 20 h / Heating 5: 96 percent / 10 N NaOH / pyridine / 3 h / Ambient temperature 6: 97 percent / 10 N NaOH / ethanol / 17 h / Heating 7: 70 percent / methanesulfonic acid / 19 h / Ambient temperature 8: NaBH4 / methanol / 0.67 h / Ambient temperature 9: p-toluenesulfonic acid / benzene / 2 h / Heating 10: 100 percent / 1-methylnaphthalene / benzene / 7 h / Heating 11: 96 percent / BBr3 / CH2Cl2 / 1.) -78 deg C, 1 h, 2.) RT, 2 h View Scheme

1: 97 percent / 10 N NaOH / ethanol / 17 h / Heating 2: 70 percent / methanesulfonic acid / 19 h / Ambient temperature 3: NaBH4 / methanol / 0.67 h / Ambient temperature 4: p-toluenesulfonic acid / benzene / 2 h / Heating 5: 100 percent / 1-methylnaphthalene / benzene / 7 h / Heating 6: 96 percent / BBr3 / CH2Cl2 / 1.) -78 deg C, 1 h, 2.) RT, 2 h View Scheme

1: 68 percent / diethyl ether; benzene / 1.) reflux, 3 h, 2.) RT, overnight 2: 100 percent / methanesulfonic acid / 1.5 h / Ambient temperature 3: 59 percent / zinc amalgam, conc. HCl / toluene; acetic acid / 27 h / Heating 4: 1.) n-BuLi / 1.) ether, hexane, -30 deg C, 1 h, 2.) ether, hexane, from -30 deg C to RT 5: 69 percent / conc,. H2SO4 / benzene / 20 h / Heating 6: 96 percent / 10 N NaOH / pyridine / 3 h / Ambient temperature 7: 97 percent / 10 N NaOH / ethanol / 17 h / Heating 8: 70 percent / methanesulfonic acid / 19 h / Ambient temperature 9: NaBH4 / methanol / 0.67 h / Ambient temperature 10: p-toluenesulfonic acid / benzene / 2 h / Heating 11: 100 percent / 1-methylnaphthalene / benzene / 7 h / Heating 12: 96 percent / BBr3 / CH2Cl2 / 1.) -78 deg C, 1 h, 2.) RT, 2 h View Scheme