sulfuric acid in water; acetic acid 48 h; Heating;

1: 70 percent / N-bromosuccinimide / CH2Cl2 / 45 h / 0 °C 2: 76 percent / 1.) cc. sulphuric acid, sodium nitrite, 2.) copper(II) sulphate pentahydrate, sodium hydrogen carbonate / H2O; acetic acid; cyclohexane / 1.) -5 deg C, 15 min; 2.) 50 deg C 3: 94 percent / n-butyllithium, zinc chloride, tetrakis(triphenylphosphine)palladium(0) / hexane; tetrahydrofuran / 20 h / Ambient temperature 4: 95 percent / H2 / 5percent palladium-on-charcoal / ethanol / 8 h 5: 70 percent / cc. sulphuric acid / H2O; acetic acid / 48 h / Heating View Scheme

1: 76 percent / 1.) cc. sulphuric acid, sodium nitrite, 2.) copper(II) sulphate pentahydrate, sodium hydrogen carbonate / H2O; acetic acid; cyclohexane / 1.) -5 deg C, 15 min; 2.) 50 deg C 2: 94 percent / n-butyllithium, zinc chloride, tetrakis(triphenylphosphine)palladium(0) / hexane; tetrahydrofuran / 20 h / Ambient temperature 3: 95 percent / H2 / 5percent palladium-on-charcoal / ethanol / 8 h 4: 70 percent / cc. sulphuric acid / H2O; acetic acid / 48 h / Heating View Scheme

1: 94 percent / n-butyllithium, zinc chloride, tetrakis(triphenylphosphine)palladium(0) / hexane; tetrahydrofuran / 20 h / Ambient temperature 2: 95 percent / H2 / 5percent palladium-on-charcoal / ethanol / 8 h 3: 70 percent / cc. sulphuric acid / H2O; acetic acid / 48 h / Heating View Scheme

1: 95 percent / H2 / 5percent palladium-on-charcoal / ethanol / 8 h 2: 70 percent / cc. sulphuric acid / H2O; acetic acid / 48 h / Heating View Scheme