lithium diisopropyl amide in tetrahydrofuran -70 deg C, 2 h, then r.t.;

1: 91 percent / sodium hydroxide / 1.33 h / 70 - 80 °C 2: 93 percent / lithium diisopropylamide / tetrahydrofuran / -70 deg C, 2 h, then r.t. View Scheme

1: 94 percent / sodium iodide / acetone / Ambient temperature 2: 91 percent / sodium hydroxide / 1.33 h / 70 - 80 °C 3: 93 percent / lithium diisopropylamide / tetrahydrofuran / -70 deg C, 2 h, then r.t. View Scheme

1: 99 percent / N-bromosuccinimide, CaCO3, benzoyl peroxide / 18 h / Heating 2: 94 percent / sodium iodide / acetone / Ambient temperature 3: 91 percent / sodium hydroxide / 1.33 h / 70 - 80 °C 4: 93 percent / lithium diisopropylamide / tetrahydrofuran / -70 deg C, 2 h, then r.t. View Scheme