hydrogen; palladium on barium sulfate in acetic acid

1: AlCl3 / CCl4 2: H2 / Pd-BaSO4 / acetic acid View Scheme

(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; magnesium 1.) ether, reflux, 0.5 h, 2.) ether, reflux, overnight; Yield givenMultistep reaction;

aluminum tri-bromide T=0°C; Einleiten von Bromwasserstoff;

in diethyl ether Heating;

(i), (ii) Al2O3, (iii) H2, Raney-Ni; Multistep reaction;

1.1: 60 percent / Br2 / CH2Cl2 / 48 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -60 °C 2.2: tetrahydrofuran; hexane / 1 h / -60 - 20 °C 3.1: p-toluenesulfonic acid / benzene / 5 h / Heating 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -70 °C 4.2: tetrahydrofuran; hexane / -70 - 20 °C 5.1: p-toluenesulfonic acid / benzene / 2 h / Heating 6.1: 97 percent / trifluoroacetic acid / H2O / Heating View Scheme

bromine in dichloromethane T=20°C; 48 h;