N-bromosuccinmide; potassium carbonate in N,N-dimethyl-formamide 0.5 h; Ambient temperature;

1: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 2: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H2O / 0.08 h / 0 °C 3: 70 percent / sodium borohydride / ethanol; H2O / 0.5 h / Ambient temperature 4: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h 5: 97 percent / iodine, nitric acid / dioxane / 3 h / Heating 6: 31 percent / 1.) triphenylphosphine, palladium(II) acetate, triethylamine / dioxane / 1 h / Heating 7: 55 percent / aq. NaOH / Ambient temperature 8: 51 percent / N-bromsuccinimide, potassium carbonate / dimethylformamide / 0.5 h / Ambient temperature 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: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H2O / 0.08 h / 0 °C 5: 70 percent / sodium borohydride / ethanol; H2O / 0.5 h / Ambient temperature 6: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h 7: 97 percent / iodine, nitric acid / dioxane / 3 h / Heating 8: 31 percent / 1.) triphenylphosphine, palladium(II) acetate, triethylamine / dioxane / 1 h / Heating 9: 55 percent / aq. NaOH / Ambient temperature 10: 51 percent / N-bromsuccinimide, potassium carbonate / dimethylformamide / 0.5 h / Ambient temperature View Scheme

1: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H2O / 0.08 h / 0 °C 2: 70 percent / sodium borohydride / ethanol; H2O / 0.5 h / Ambient temperature 3: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h 4: 97 percent / iodine, nitric acid / dioxane / 3 h / Heating 5: 31 percent / 1.) triphenylphosphine, palladium(II) acetate, triethylamine / dioxane / 1 h / Heating 6: 55 percent / aq. NaOH / Ambient temperature 7: 51 percent / N-bromsuccinimide, potassium carbonate / dimethylformamide / 0.5 h / Ambient temperature 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: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H2O / 0.08 h / 0 °C 4: 70 percent / sodium borohydride / ethanol; H2O / 0.5 h / Ambient temperature 5: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h 6: 97 percent / iodine, nitric acid / dioxane / 3 h / Heating 7: 31 percent / 1.) triphenylphosphine, palladium(II) acetate, triethylamine / dioxane / 1 h / Heating 8: 55 percent / aq. NaOH / Ambient temperature 9: 51 percent / N-bromsuccinimide, potassium carbonate / dimethylformamide / 0.5 h / Ambient temperature View Scheme

1: 55 percent / aq. NaOH / Ambient temperature 2: 51 percent / N-bromsuccinimide, potassium carbonate / dimethylformamide / 0.5 h / Ambient temperature View Scheme

1: 97 percent / iodine, nitric acid / dioxane / 3 h / Heating 2: 31 percent / 1.) triphenylphosphine, palladium(II) acetate, triethylamine / dioxane / 1 h / Heating 3: 55 percent / aq. NaOH / Ambient temperature 4: 51 percent / N-bromsuccinimide, potassium carbonate / dimethylformamide / 0.5 h / Ambient temperature View Scheme

1: 31 percent / 1.) triphenylphosphine, palladium(II) acetate, triethylamine / dioxane / 1 h / Heating 2: 55 percent / aq. NaOH / Ambient temperature 3: 51 percent / N-bromsuccinimide, potassium carbonate / dimethylformamide / 0.5 h / Ambient temperature View Scheme

1: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h 2: 97 percent / iodine, nitric acid / dioxane / 3 h / Heating 3: 31 percent / 1.) triphenylphosphine, palladium(II) acetate, triethylamine / dioxane / 1 h / Heating 4: 55 percent / aq. NaOH / Ambient temperature 5: 51 percent / N-bromsuccinimide, potassium carbonate / dimethylformamide / 0.5 h / Ambient temperature View Scheme