sodium hydroxide in tetrahydrofuran; water T=0°C;

1: pyridine / acetonitrile 2: KH / dimethylformamide 3: HBr 4: KOH / methanol View Scheme

1: pyridine / acetonitrile 2: KH / dimethylformamide 3: HBr View Scheme

1: 65 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / CH2Cl2 / 2 h / Ambient temperature 2: 1.) sodium hydride / 1.) DMF, 80 deg C, 2.5 h, 2.) DMF, 80 deg C, 24 h View Scheme

1: 65 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / CH2Cl2 / 2 h / Ambient temperature 2: 1.) sodium hydride / 1.) DMF, 80 deg C, 2.5 h, 2.) DMF, 80 deg C, 24 h 3: 86 percent / phenol, 33percent HBr in acetic acid / 60 h / 80 °C View Scheme