hydrogenchloride; iron in ethanol; water 2 h; Reflux;

hydrogenchloride; potassium hydroxide; N,N,N',N,-tetramethylethylenediamine; bromine; tert.-butyl lithium; sodium thiosulfate in tetrahydrofuran; ethanol; hexane; ethyl acetate; pentane

sodium hydroxide in ethanol 2 h; Reflux;

hydrogenchloride in ethanol; water Reflux;

sodium hydroxide; bromine 1) 4 h, 0 deg C 2) 3 h, 60 deg C;

1: 1) t-BuLi, tetramethylethylenediamine 2) Br2 / 1) THF, pentane, -70 deg C, 60 min 2) -70 deg C, 30 min 2: 2.5N aq. NaOH / ethanol / 1 h / 80 °C View Scheme

1: 83 percent / Na2CO3 / diethyl ether / 1 h / -10 °C 2: 1) t-BuLi, tetramethylethylenediamine 2) Br2 / 1) THF, pentane, -70 deg C, 60 min 2) -70 deg C, 30 min 3: 2.5N aq. NaOH / ethanol / 1 h / 80 °C View Scheme

1: 1) 10M NaOH 2) 30percent aq. H2O2 / 1) 70 deg C, 60 min 2) 70 deg C, 60 min 2: 1) 48percent HBr, NaNO2 2) CuBr / 1) water, 1 h, 0 deg C 2) a) 30 min, r.t. b) 90 min, 70 deg C 3: SOCl2 / CH2Cl2 / 1 h / Heating 4: NH3-gas / CH2Cl2 / 1 h 5: 79 percent / Br2, NaOH / 1) 4 h, 0 deg C 2) 3 h, 60 deg C View Scheme

1: 96 percent / Na2SO4, NH2OH*HCl, conc. HCl / H2O / 0.17 h / Heating 2: 55 percent / conc. H2SO4 / 0.75 h / 70 °C 3: 1) 10M NaOH 2) 30percent aq. H2O2 / 1) 70 deg C, 60 min 2) 70 deg C, 60 min 4: 1) 48percent HBr, NaNO2 2) CuBr / 1) water, 1 h, 0 deg C 2) a) 30 min, r.t. b) 90 min, 70 deg C 5: SOCl2 / CH2Cl2 / 1 h / Heating 6: NH3-gas / CH2Cl2 / 1 h 7: 79 percent / Br2, NaOH / 1) 4 h, 0 deg C 2) 3 h, 60 deg C View Scheme

1: 55 percent / conc. H2SO4 / 0.75 h / 70 °C 2: 1) 10M NaOH 2) 30percent aq. H2O2 / 1) 70 deg C, 60 min 2) 70 deg C, 60 min 3: 1) 48percent HBr, NaNO2 2) CuBr / 1) water, 1 h, 0 deg C 2) a) 30 min, r.t. b) 90 min, 70 deg C 4: SOCl2 / CH2Cl2 / 1 h / Heating 5: NH3-gas / CH2Cl2 / 1 h 6: 79 percent / Br2, NaOH / 1) 4 h, 0 deg C 2) 3 h, 60 deg C View Scheme