tetrabutylammomium bromide; nitric acid in dichloromethane T=20°C; 24 h;

tert.-butylhydroperoxide; potassium tert-butylate in ammonia T=-33°C;

sodium hydroxide 5 h; Reflux;

sodium hydroxide 72 h; Heating;

iron; acetic acid in water 0.166667 h; Heating;

1: 90 percent / Cs2CO3 / dimethylformamide / 16 h / 20 °C 2: 82 percent / t-BuOK / dimethylformamide / 0.5 h / -20 - -10 °C 3: 30 percent / H2 / PtO2 / ethanol / 2 h / 20 °C / 1551.44 - 1810.02 Torr 4: 85 percent / ammonium formate / Pd/C / methanol / 20 °C View Scheme

sodium hydroxide