lithium iodide in pyridine 8 h; Heating;

1: 45 percent / sodium hydride / tetrahydrofuran / 12 h / Heating 2: 91 percent / lithium iodide / pyridine / 8 h / Heating View Scheme

1: N-bromosuccinimide / CCl4 2: 45 percent / sodium hydride / tetrahydrofuran / 12 h / Heating 3: 91 percent / lithium iodide / pyridine / 8 h / Heating View Scheme

1: 1) NaOH / 1) H2O, reflux, 2) reflux, 4 h 2: 79 percent / N-bromosuccinimide, azobisisobutyronitrile / CCl4 / 1.5 h / Heating 3: 52 percent / NaH / tetrahydrofuran / 12 h / Heating 4: 86 percent / anhydr. LiI / pyridine / 8 h / Heating View Scheme

1: NaH / tetrahydrofuran 2: LiI / pyridine / Heating View Scheme

Yield given. Multistep reaction;