hydrogenchloride in water 48 h; Ambient temperature;

1: NaBH(AcO)3, CH3COOH / 1,2-dichloro-ethane / 24 h / Ambient temperature 2: 2.634 g / conc. aq. HCl / 48 h / Ambient temperature View Scheme

1: NaBH(AcO)3, CH3COOH / 1,2-dichloro-ethane / 24 h / Ambient temperature 2: 2.634 g / conc. aq. HCl / 48 h / Ambient temperature View Scheme

1: With lithium diisopropyl amide in tetrahydrofuran T=-78°C; 1 h; 2: With 1,1-dibromo-tetrachloro-ethane in tetrahydrofuran T=-90°C; 0.5 h;

1.1: lithium diisopropylamide / tetrahydrofuran / 1 h / -78 °C 1.2: 66 percent / dibromotetrachlorethane / tetrahydrofuran / 0.5 h / -90 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 1.75 h / -78 °C 2.2: 36 percent / tetrahydrofuran; hexane / 3.25 h / -78 - 20 °C 3.1: 67 percent / piperidine; CuI / Pd(P(C6H5)3)4 / tetrahydrofuran / 3.5 h / 40 °C View Scheme

1.1: lithium diisopropylamide / tetrahydrofuran / 1 h / -78 °C 1.2: 66 percent / dibromotetrachlorethane / tetrahydrofuran / 0.5 h / -90 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 1.75 h / -78 °C 2.2: 36 percent / tetrahydrofuran; hexane / 3.25 h / -78 - 20 °C 3.1: 7 percent / piperidine; CuI / Pd(P(C6H5)3)4 / tetrahydrofuran / 3.5 h / 40 °C View Scheme