boron trifluoride diethyl etherate in dichloromethane T=0 - 5°C;

in neat (no solvent) T=250°C; 0.333333 h;

1: H2, 1percent aq. NaOH / Pd/C / H2O / Ambient temperature 2: 1.) NaNO2, HCl 3: 1.) SnCl2, conc. HCl; 2.) 2.5percent HCl / 1.) 15 h; 2.) reflux, 5 min 4: 15.5 g / p.toluenesulfonic acid / benzene / 6 h / Heating 5: Na / various solvent(s) / 1 h / Heating 6: 83 percent / NaOH / ethanol / 2.5 h / Heating 7: 80 percent / neat (no solvent) / 0.33 h / 250 °C View Scheme

1: 15.5 g / p.toluenesulfonic acid / benzene / 6 h / Heating 2: Na / various solvent(s) / 1 h / Heating 3: 83 percent / NaOH / ethanol / 2.5 h / Heating 4: 80 percent / neat (no solvent) / 0.33 h / 250 °C View Scheme

1: 15.5 g / p.toluenesulfonic acid / benzene / 6 h / Heating 2: Na / various solvent(s) / 1 h / Heating 3: 83 percent / NaOH / ethanol / 2.5 h / Heating 4: 80 percent / neat (no solvent) / 0.33 h / 250 °C View Scheme

1: 1.) NaNO2, HCl 2: 1.) SnCl2, conc. HCl; 2.) 2.5percent HCl / 1.) 15 h; 2.) reflux, 5 min 3: 15.5 g / p.toluenesulfonic acid / benzene / 6 h / Heating 4: Na / various solvent(s) / 1 h / Heating 5: 83 percent / NaOH / ethanol / 2.5 h / Heating 6: 80 percent / neat (no solvent) / 0.33 h / 250 °C View Scheme

1: Na / various solvent(s) / 1 h / Heating 2: 83 percent / NaOH / ethanol / 2.5 h / Heating 3: 80 percent / neat (no solvent) / 0.33 h / 250 °C View Scheme

1: 1.) SnCl2, conc. HCl; 2.) 2.5percent HCl / 1.) 15 h; 2.) reflux, 5 min 2: 15.5 g / p.toluenesulfonic acid / benzene / 6 h / Heating 3: Na / various solvent(s) / 1 h / Heating 4: 83 percent / NaOH / ethanol / 2.5 h / Heating 5: 80 percent / neat (no solvent) / 0.33 h / 250 °C View Scheme

1: 83 percent / NaOH / ethanol / 2.5 h / Heating 2: 80 percent / neat (no solvent) / 0.33 h / 250 °C View Scheme

1: 60percent aq. AcOH / Ambient temperature 2: 36 percent / DMSO, oxalyl chloride, Et3N / CH2Cl2 / 0.83 h / -60 °C 3: 90 percent / BF3*OEt2 / CH2Cl2 / 0.5 h / 0 - 5 °C View Scheme