sodium nitrite in sulfuric acid; water

bromine in chloroform T=0 - 20°C; 13 h;

1: 59 percent / NaOMe / dimethylformamide / 0 deg C to r.t., overnight 2: 95.46 percent / N2H4*H2O / 5 percent Ru/C / ethanol / 1) 65 deg C to 70 deg C, 2) reflux, 7 h 3: 1) aq. NaNO2, H2SO4 / 1) 0 deg C, 2 h, 2) r.t., overnight, 70 deg C, 24 h View Scheme

1: 95.46 percent / N2H4*H2O / 5 percent Ru/C / ethanol / 1) 65 deg C to 70 deg C, 2) reflux, 7 h 2: 1) aq. NaNO2, H2SO4 / 1) 0 deg C, 2 h, 2) r.t., overnight, 70 deg C, 24 h View Scheme

tetrachloromethane; bromine; acetic acid