Sodium bromate; sodium hydrogensulfite in chloroform 1.5 h;

1: CF3SO3H / CH2Cl2 / -15 °C 2: 18 percent / H2O / acetone 3: NaBH4 4: CF3COOH / CH2Cl2 / 0.17 h / -20 °C 5: H2O / acetone View Scheme

potassium tert-butylate in tetrahydrofuran; chloroform

sodium methylate in methanol; dichloromethane T=-10°C; 1 h;

dihydrogen peroxide; iodine in chlororform; chloroform

sodium chlorate; iodine in chloroform; water

dihydrogen peroxide; iodine in water

1: 92 percent / p-toluenesulfonic acid / 1.) 5 deg C, 2.) RT, 10 min 2: 1.) n-BuLi / 1.) ether, hexane, RT, 15 min, 2.) 22 deg C, 1 h 3: 72 percent / H2, potassium carbonate / Lindlar catalyst / toluene / 3 h / 20 °C / 760 Torr 4: PBr3 / diethyl ether / 0.08 h / Ambient temperature 5: 69 percent / benzene / Heating 6: 78 percent / NaOCH3 / CH2Cl2; methanol / 1 h / -10 °C View Scheme

1: 1.) LDA / 1.) THF, hexane, -60 deg C, 90 min, 2.) a) 3 min, b) RT, 2 h 2: 85 percent / NaH / methanol / 3 h / Heating 3: 91 percent / p-toluenesulfonic acid / benzene / 3 h / Heating 4: 1.) n-BuLi / 1.) ether, hexane, RT, 15 min, 2.) 22 deg C, 1 h 5: 72 percent / H2, potassium carbonate / Lindlar catalyst / toluene / 3 h / 20 °C / 760 Torr 6: PBr3 / diethyl ether / 0.08 h / Ambient temperature 7: 69 percent / benzene / Heating 8: 78 percent / NaOCH3 / CH2Cl2; methanol / 1 h / -10 °C View Scheme

1: 85 percent / NaH / methanol / 3 h / Heating 2: 91 percent / p-toluenesulfonic acid / benzene / 3 h / Heating 3: 1.) n-BuLi / 1.) ether, hexane, RT, 15 min, 2.) 22 deg C, 1 h 4: 72 percent / H2, potassium carbonate / Lindlar catalyst / toluene / 3 h / 20 °C / 760 Torr 5: PBr3 / diethyl ether / 0.08 h / Ambient temperature 6: 69 percent / benzene / Heating 7: 78 percent / NaOCH3 / CH2Cl2; methanol / 1 h / -10 °C View Scheme