1: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 2: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min 3: 66 percent / potassium permanganate / H2O / 3 h / Heating 4: 99 percent / diethyl ether / 1.) 0 deg C, 2.) RT, overnight 5: 70 percent / LAH / diethyl ether / 0.5 h / -78 °C 6: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) methylene chloride, -60 deg C, 20 min, 2.) from -60 deg C to RT View Scheme

1: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 2: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min 3: 66 percent / potassium permanganate / H2O / 3 h / Heating View Scheme

1: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 2: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min 3: 66 percent / potassium permanganate / H2O / 3 h / Heating 4: 99 percent / diethyl ether / 1.) 0 deg C, 2.) RT, overnight 5: 70 percent / LAH / diethyl ether / 0.5 h / -78 °C View Scheme