ammonium chloride; aluminium trichloride T=185°C; 15 h;

borane in tetrahydrofuran 18 h; Heating;

1: SOCl2, DMF / toluene / 2.5 h / 55 - 60 °C 2: NaN3 / acetone; H2O / 0.17 h / 0 °C 3: toluene / 0.5 h / Heating 4: AlCl3 / tetrachloroethene / 3 h / 70 - 75 °C 5: 1M BH3 / tetrahydrofuran / 18 h / Heating View Scheme

1: NaN3 / acetone; H2O / 0.17 h / 0 °C 2: toluene / 0.5 h / Heating 3: AlCl3 / tetrachloroethene / 3 h / 70 - 75 °C 4: 1M BH3 / tetrahydrofuran / 18 h / Heating View Scheme

1: 1.) NaNO2, 48percent HBr, 2.) CuBr / 1.) acetone, H2O, -5 deg C, 30 min, 2.) acetone, H2O, 25 deg C, 30 min 2: Zn, acetic acid / 0.5 h 3: 10percent aq. NaOH / 2 h / Heating 4: SOCl2, DMF / toluene / 2.5 h / 55 - 60 °C 5: NaN3 / acetone; H2O / 0.17 h / 0 °C 6: toluene / 0.5 h / Heating 7: AlCl3 / tetrachloroethene / 3 h / 70 - 75 °C 8: 1M BH3 / tetrahydrofuran / 18 h / Heating View Scheme

1: AlCl3 / tetrachloroethene / 3 h / 70 - 75 °C 2: 1M BH3 / tetrahydrofuran / 18 h / Heating View Scheme

1: 10percent aq. NaOH / 2 h / Heating 2: SOCl2, DMF / toluene / 2.5 h / 55 - 60 °C 3: NaN3 / acetone; H2O / 0.17 h / 0 °C 4: toluene / 0.5 h / Heating 5: AlCl3 / tetrachloroethene / 3 h / 70 - 75 °C 6: 1M BH3 / tetrahydrofuran / 18 h / Heating View Scheme

1: Zn, acetic acid / 0.5 h 2: 10percent aq. NaOH / 2 h / Heating 3: SOCl2, DMF / toluene / 2.5 h / 55 - 60 °C 4: NaN3 / acetone; H2O / 0.17 h / 0 °C 5: toluene / 0.5 h / Heating 6: AlCl3 / tetrachloroethene / 3 h / 70 - 75 °C 7: 1M BH3 / tetrahydrofuran / 18 h / Heating View Scheme