1: 85 percent / NH3 / benzene / 10 °C 2: 70 percent / Br2, NaOH / various solvent(s) / 1) 0-5 deg C, 20 min; 2) 70 deg C, 1 h View Scheme

1 h; Heating / reflux;

thionyl chloride 2 h; Heating;

1: aq. NaOH; HgO 2: 22 percent / SOCl2 View Scheme

1: 10percent NaOH / methanol / 1 h / Heating 2: SOCl2 / 1 h / Heating View Scheme

sodium hydroxide; phosphorus pentachloride; mercury(II) oxide 1.) water, acetic acid, reflux, 98 h; 2.) EtOAc, r.t.; Multistep reaction. Title compound not separated from byproducts;

ammonia in benzene T=10°C;

1: 85 percent / NH3 / benzene / 10 °C 2: 70 percent / Br2, NaOH / various solvent(s) / 1) 0-5 deg C, 20 min; 2) 70 deg C, 1 h 3: NaNO2, conc. aq. HCl / H2O / 0.33 h / 10 °C 4: I2, KI / aq. HCl / 1 h / 80 °C 5: 72 percent / various solvent(s) / 4 h / 140 °C View Scheme

1: 85 percent / NH3 / benzene / 10 °C 2: 70 percent / Br2, NaOH / various solvent(s) / 1) 0-5 deg C, 20 min; 2) 70 deg C, 1 h 3: NaNO2, conc. aq. HCl / H2O / 0.33 h / 10 °C 4: I2, KI / aq. HCl / 1 h / 80 °C 5: 72 percent / various solvent(s) / 4 h / 140 °C 6: 78 percent / 80percent aq. H2O2, trifluoroacetic anhydride / 1) 0 deg C, 1 h; 2) 20 deg C, 30 min View Scheme

1: 85 percent / NH3 / benzene / 10 °C 2: 70 percent / Br2, NaOH / various solvent(s) / 1) 0-5 deg C, 20 min; 2) 70 deg C, 1 h 3: NaNO2, conc. aq. HCl / H2O / 0.33 h / 10 °C 4: I2, KI / aq. HCl / 1 h / 80 °C 5: 72 percent / various solvent(s) / 4 h / 140 °C 6: 78 percent / 80percent aq. H2O2, trifluoroacetic anhydride / 1) 0 deg C, 1 h; 2) 20 deg C, 30 min 7: 68 percent / CrO3 / acetic acid / 0.67 h / 70 °C View Scheme