1: With lithium aluminium tetrahydride in tetrahydrofuran 18 h; Inert atmosphere; 2: With hydrogenchloride; water in tetrahydrofuran

potassium hydroxide in methanol

potassium hydroxide; water in methanol 7 h; Heating;

1: 64 percent / Br2 / CHCl3 / 1.) 0-10 deg C, 2 h, 2.) refrigerator, 16 h 2: 93 percent / acetone; H2O / 10 h / Heating 3: 81 percent / dimethylformamide / 10 h / heating on a steam-bath 4: 94 percent / KOH, H2O / methanol / 7 h / Heating View Scheme

1: 60 percent / NaBH4 / methanol / 19 h / Ambient temperature 2: 95 percent / dioxane / 15 h / Heating; heating with KHSO4; ring contraction of 1-benzothiepin derivatives to 1-benzothiophens 3: 81 percent / dimethylformamide / 10 h / heating on a steam-bath 4: 94 percent / KOH, H2O / methanol / 7 h / Heating View Scheme

1: 81 percent / dimethylformamide / 10 h / heating on a steam-bath 2: 94 percent / KOH, H2O / methanol / 7 h / Heating View Scheme

1: 93 percent / acetone; H2O / 10 h / Heating 2: 81 percent / dimethylformamide / 10 h / heating on a steam-bath 3: 94 percent / KOH, H2O / methanol / 7 h / Heating View Scheme

1: 95 percent / dioxane / 15 h / Heating; heating with KHSO4; ring contraction of 1-benzothiepin derivatives to 1-benzothiophens 2: 81 percent / dimethylformamide / 10 h / heating on a steam-bath 3: 94 percent / KOH, H2O / methanol / 7 h / Heating View Scheme

palladium; acetic acid Hydrogenation;

1: pyridine 2: palladium; acetic acid / Hydrogenation View Scheme