1: NaNO2, conc. aq. HCl / H2O / 0.33 h / 10 °C 2: I2, KI / aq. HCl / 1 h / 80 °C 3: 72 percent / various solvent(s) / 4 h / 140 °C 4: 78 percent / 80percent aq. H2O2, trifluoroacetic anhydride / 1) 0 deg C, 1 h; 2) 20 deg C, 30 min 5: 68 percent / CrO3 / acetic acid / 0.67 h / 70 °C 6: 81 percent / SnCl2*2H2O, conc. aq. HCl / ethanol / 2 h / 100 °C 7: 1) nitrosylsulfuric acid; 2) SnCl2*2H2O, conc. aq. HCl / 1) acetic acid, 20 deg C, 3 h; 2) 10 deg C, 1 h View Scheme

1: NaNO2, conc. aq. HCl / H2O / 0.33 h / 10 °C 2: I2, KI / aq. HCl / 1 h / 80 °C 3: 72 percent / various solvent(s) / 4 h / 140 °C 4: 82 percent / SnCl2*2H2O, conc. aq. HCl / ethanol / 2 h / 100 °C 5: 1) nitrosylsulfuric acid; 2) SnCl2*2H2O, conc. aq. HCl / 1) acetic acid, 20 deg C, 3 h; 2) 10 deg C, 1 h 6: 2) BF3 etherate / 1) 70 deg C, 4 h; 2) acetic acid, reflux, 3 h View Scheme

1: NaNO2, conc. aq. HCl / H2O / 0.33 h / 10 °C 2: I2, KI / aq. HCl / 1 h / 80 °C 3: 72 percent / various solvent(s) / 4 h / 140 °C 4: 78 percent / 80percent aq. H2O2, trifluoroacetic anhydride / 1) 0 deg C, 1 h; 2) 20 deg C, 30 min 5: 68 percent / CrO3 / acetic acid / 0.67 h / 70 °C 6: 81 percent / SnCl2*2H2O, conc. aq. HCl / ethanol / 2 h / 100 °C 7: 1) nitrosylsulfuric acid; 2) SnCl2*2H2O, conc. aq. HCl / 1) acetic acid, 20 deg C, 3 h; 2) 10 deg C, 1 h 8: 2) BF3 etherate / 1) 70 deg C, 4 h; 2) acetic acid, reflux, 3 h View Scheme

1: NaNO2, conc. aq. HCl / H2O / 0.33 h / 10 °C 2: I2, KI / aq. HCl / 1 h / 80 °C 3: 72 percent / various solvent(s) / 4 h / 140 °C 4: 82 percent / SnCl2*2H2O, conc. aq. HCl / ethanol / 2 h / 100 °C 5: 1) nitrosylsulfuric acid; 2) SnCl2*2H2O, conc. aq. HCl / 1) acetic acid, 20 deg C, 3 h; 2) 10 deg C, 1 h 6: 2) BF3 etherate / 1) 70 deg C, 4 h; 2) acetic acid, reflux, 3 h 7: 93 percent / 6 h / 75 °C View Scheme

1: (i) H2SO4, (ii) aq. NaNO2, (iii) CuCl, aq. HCl 2: Fe, aq. HCl / ethanol / Heating View Scheme

ueber die Diazonium-Verbindung;

1: chloroform; bromine 2: concentrated H2SO4; glacial acetic acid / Diazotization.Behandlung der Diazoniumsalz-Loesung mit Cu2O in Aethanol 3: aqueous ethanol; sodium dithionite View Scheme

hydrogenchloride Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuCl in wss. HCl;

(i) NaNO2, aq. HCl, acetone, (ii) aq. NaBF4, (iii) CuCl, aq. HCl; Multistep reaction;