hydrogenchloride in ethanol 6 h; Heating;

1: NaNO2, 48percent HBF4 / H2O / 1 h / -10 °C 2: 80 percent / toluene / 1.) 100 deg C; 2.) reflux, 1 h. 3: 81 percent / 6 M hydrochloric acid / ethanol / 6 h / Heating View Scheme

1: 93 percent / xylene / 2 h / Heating 2: 80 percent / various solvent(s) / Heating 3: 96 percent / K2CO3 / dimethylformamide / 4.5 h / 100 °C 4: 99 percent / 1.0 N aq. NaOH / ethanol / 1.) 100 deg C, 1 h; 2.) room temp., 18 h. 5: 90 percent / thionyl chloride / 1.) room temp., 20 min.; 2.) 60 deg C, 6 h. 6: 98 percent / aq. NaOH / 1.)room temp., 20 min; 2.) 100 deg C, 2 h. 7: 98 percent / POCl3 / 1 h / Heating View Scheme