aluminum tri-bromide in acetonitrile T=50°C;

1: K2CO3 / dimethylformamide / 3 h / Heating 2: conc.HCl / acetic acid / 1.42 h / Ambient temperature 3: pyridine / 2 h / 120 °C 4: KOH, pyridine / 4 h / 60 °C 5: 97 percent / sodium acetate / acetic acid / 4 h / 140 °C 6: 91 percent / H2 / 10percent Pd/C / ethyl acetate; methanol 7: AlBr3 / acetonitrile / 50 °C View Scheme

1: pyridine / 2 h / 120 °C 2: KOH, pyridine / 4 h / 60 °C 3: 97 percent / sodium acetate / acetic acid / 4 h / 140 °C 4: 91 percent / H2 / 10percent Pd/C / ethyl acetate; methanol 5: AlBr3 / acetonitrile / 50 °C View Scheme

1: conc.HCl / acetic acid / 1.42 h / Ambient temperature 2: pyridine / 2 h / 120 °C 3: KOH, pyridine / 4 h / 60 °C 4: 97 percent / sodium acetate / acetic acid / 4 h / 140 °C 5: 91 percent / H2 / 10percent Pd/C / ethyl acetate; methanol 6: AlBr3 / acetonitrile / 50 °C View Scheme

1: 91 percent / H2 / 10percent Pd/C / ethyl acetate; methanol 2: AlBr3 / acetonitrile / 50 °C View Scheme

1: 97 percent / sodium acetate / acetic acid / 4 h / 140 °C 2: 91 percent / H2 / 10percent Pd/C / ethyl acetate; methanol 3: AlBr3 / acetonitrile / 50 °C View Scheme

1: KOH, pyridine / 4 h / 60 °C 2: 97 percent / sodium acetate / acetic acid / 4 h / 140 °C 3: 91 percent / H2 / 10percent Pd/C / ethyl acetate; methanol 4: AlBr3 / acetonitrile / 50 °C View Scheme