NOBF4; acetic acid in dichloromethane; acetonitrile

sulfuric acid in water T=150°C; 2 h;

1: 84 percent / Br2 / acetic acid / 1 h / Ambient temperature 2: 1.) conc. H2SO4, NaNO2, 2.) 50percent H3PO2, Cu2O / 1.) H2O, -2 deg C - -3 deg C, 105 min, 2.) H2O, -5 deg C, 90 min; 0 deg C, 10 min 3: 63 percent / dimethylformamide / 5 h / Heating 4: 92 percent / 75percent H2SO4 / H2O / 2 h / 150 °C View Scheme

1: 63 percent / dimethylformamide / 5 h / Heating 2: 92 percent / 75percent H2SO4 / H2O / 2 h / 150 °C View Scheme

1: 1.) conc. H2SO4, NaNO2, 2.) 50percent H3PO2, Cu2O / 1.) H2O, -2 deg C - -3 deg C, 105 min, 2.) H2O, -5 deg C, 90 min; 0 deg C, 10 min 2: 63 percent / dimethylformamide / 5 h / Heating 3: 92 percent / 75percent H2SO4 / H2O / 2 h / 150 °C View Scheme

1: thionyl chloride / methanol 2: ammonium chloride / ethanol View Scheme

thionyl chloride in methanol

thionyl chloride T=0 - 20°C; 6 h; Inert atmosphere;