1: oxalyl chloride / 13 h / 20 - 45 °C 2: 0.50 g / 1 h / Heating View Scheme

1: 54.5 percent / HCl / 9 h / Heating 2: 100 percent / Et3N / CHCl3 / 5 h / Ambient temperature 3: 84.5 percent / DIBAL / toluene / 0.5 h / -70 °C 4: 83.8 percent / piperidine / benzene / 22 h / Heating 5: 99.5 percent / H2 / Pd / tetrahydrofuran; methanol / 5 h / 760 Torr / Ambient temperature 6: 50percent aq. NaOH / 2 h / Heating 7: benzene / 2 h / Heating 8: 96.6 percent / 50percent aq. AcOH / 0.5 h / Heating View Scheme

sulfuric acid Reflux;

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / acetonitrile / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 20 °C View Scheme

1: sulfuric acid / Reflux 2: bromine / chloroform / 20 °C View Scheme

1: sulfuric acid / Reflux 2: bromine / chloroform / 20 °C View Scheme

1.1: thionyl chloride / 12 h / 0 °C / Reflux 1.2: pH 9 2.1: 4-(N,N-dimethlyamino)pyridine / tert-butyl alcohol; acetone / 18 h / 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 6.5 h / 0 °C / Inert atmosphere View Scheme