iodine; nitric acid in 1,4-dioxane 3 h; Heating;

1: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 2: 1.) red mercuric oxide, mercuric chloride, 2.) sodium borohydride / 1.) aq. THF, RT 90 min, 2.) ethanol, water, RT, 30 min 3: 77 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h 4: 66 percent / nitric acid, iodine / dioxane / 3 h / Heating View Scheme

1: 1.) hexamethylphosphoramide (HMPA), n-butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.) 90 min 2: 90 percent / trifluoroacetic acid / butan-1-ol / 0.17 h / Ambient temperature 3: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 4: 1.) red mercuric oxide, mercuric chloride, 2.) sodium borohydride / 1.) aq. THF, RT 90 min, 2.) ethanol, water, RT, 30 min 5: 77 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h 6: 66 percent / nitric acid, iodine / dioxane / 3 h / Heating View Scheme

1: 1.) red mercuric oxide, mercuric chloride, 2.) sodium borohydride / 1.) aq. THF, RT 90 min, 2.) ethanol, water, RT, 30 min 2: 77 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h 3: 66 percent / nitric acid, iodine / dioxane / 3 h / Heating View Scheme

1: 90 percent / trifluoroacetic acid / butan-1-ol / 0.17 h / Ambient temperature 2: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 3: 1.) red mercuric oxide, mercuric chloride, 2.) sodium borohydride / 1.) aq. THF, RT 90 min, 2.) ethanol, water, RT, 30 min 4: 77 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h 5: 66 percent / nitric acid, iodine / dioxane / 3 h / Heating View Scheme