potassium fluoride in dimethyl sulfoxide T=150°C; 3 h;

1: 80 percent / 1.) DIBAH, 2.) pyridine, 3.) bromine / diethyl ether; CH2Cl2 / 1.) 5 to 40 deg C, 3.5 h, 2.) 0 deg C, 3.) -78 deg C 2: 82 percent / bromine / diethyl ether; pyridine; CH2Cl2 / 4 h / 30 °C / Irradiation 3: 75 percent / 1.) sec-BuLi / tetrahydrofuran; cyclohexane / 1.) -78 deg C, 4 min, 2.) -78 deg C to RT, 2 h 4: 78 percent / anhydr. KF / dimethylsulfoxide / 3 h / 150 °C View Scheme

1: 82 percent / bromine / diethyl ether; pyridine; CH2Cl2 / 4 h / 30 °C / Irradiation 2: 75 percent / 1.) sec-BuLi / tetrahydrofuran; cyclohexane / 1.) -78 deg C, 4 min, 2.) -78 deg C to RT, 2 h 3: 78 percent / anhydr. KF / dimethylsulfoxide / 3 h / 150 °C View Scheme

1: 75 percent / 1.) sec-BuLi / tetrahydrofuran; cyclohexane / 1.) -78 deg C, 4 min, 2.) -78 deg C to RT, 2 h 2: 78 percent / anhydr. KF / dimethylsulfoxide / 3 h / 150 °C View Scheme

in tetrahydrofuran; water; acetic acid T=45°C; 6 h;