hydrogen bromide in water T=140°C; 4 h;

hydrogen; palladium on activated charcoal in acetic acid

1: lithium diisopropylamide / tetrahydrofuran 2: 25percent sulfuric acid, 8N chromic acid / acetone 3: KOH / ethanol; H2O / 6 h / Heating 4: 74 percent / acetic anhydride / 3 h / Heating 5: 2.) acetic anhydride / 1.) benzene, 1 h, reflux; 2.) 5 h, reflux 6: 94 percent / boron tribromide / CH2Cl2 / 2 h / Ambient temperature 7: 77 percent / potassium carbonate / dimethylformamide 8: 78 percent / LiAlH4 / tetrahydrofuran / Heating 9: 85 percent / H2 / 10percent Pd-C / acetic acid View Scheme

1: 74 percent / acetic anhydride / 3 h / Heating 2: 2.) acetic anhydride / 1.) benzene, 1 h, reflux; 2.) 5 h, reflux 3: 94 percent / boron tribromide / CH2Cl2 / 2 h / Ambient temperature 4: 77 percent / potassium carbonate / dimethylformamide 5: 78 percent / LiAlH4 / tetrahydrofuran / Heating 6: 85 percent / H2 / 10percent Pd-C / acetic acid View Scheme

1: 2.) acetic anhydride / 1.) benzene, 1 h, reflux; 2.) 5 h, reflux 2: 94 percent / boron tribromide / CH2Cl2 / 2 h / Ambient temperature 3: 77 percent / potassium carbonate / dimethylformamide 4: 78 percent / LiAlH4 / tetrahydrofuran / Heating 5: 85 percent / H2 / 10percent Pd-C / acetic acid View Scheme

1: KOH / ethanol; H2O / 6 h / Heating 2: 74 percent / acetic anhydride / 3 h / Heating 3: 2.) acetic anhydride / 1.) benzene, 1 h, reflux; 2.) 5 h, reflux 4: 94 percent / boron tribromide / CH2Cl2 / 2 h / Ambient temperature 5: 77 percent / potassium carbonate / dimethylformamide 6: 78 percent / LiAlH4 / tetrahydrofuran / Heating 7: 85 percent / H2 / 10percent Pd-C / acetic acid View Scheme

1: 25percent sulfuric acid, 8N chromic acid / acetone 2: KOH / ethanol; H2O / 6 h / Heating 3: 74 percent / acetic anhydride / 3 h / Heating 4: 2.) acetic anhydride / 1.) benzene, 1 h, reflux; 2.) 5 h, reflux 5: 94 percent / boron tribromide / CH2Cl2 / 2 h / Ambient temperature 6: 77 percent / potassium carbonate / dimethylformamide 7: 78 percent / LiAlH4 / tetrahydrofuran / Heating 8: 85 percent / H2 / 10percent Pd-C / acetic acid View Scheme

1: 77 percent / potassium carbonate / dimethylformamide 2: 78 percent / LiAlH4 / tetrahydrofuran / Heating 3: 85 percent / H2 / 10percent Pd-C / acetic acid View Scheme

1: 94 percent / boron tribromide / CH2Cl2 / 2 h / Ambient temperature 2: 77 percent / potassium carbonate / dimethylformamide 3: 78 percent / LiAlH4 / tetrahydrofuran / Heating 4: 85 percent / H2 / 10percent Pd-C / acetic acid View Scheme

1: 78 percent / LiAlH4 / tetrahydrofuran / Heating 2: 85 percent / H2 / 10percent Pd-C / acetic acid View Scheme