sodium tetrahydroborate in tetrahydrofuran 1 h; Ambient temperature;

1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 2.1: sodium acetate / ethanol / 1 h / 80 °C 3.1: 1,2-dichloro-benzene / 1 h / Inert atmosphere; Heating; Microwave irradiation 4.1: palladium 10 on activated carbon / 1,2-dichloro-benzene / 180 °C 5.1: 12 h / 20 °C 5.2: 0.5 h / 20 °C 6.1: Jone's reagent / acetone / 0.5 h / 0 °C 6.2: Cooling with ice View Scheme

sodium hydroxide; silver nitrate in water; acetonitrile T=20°C; 16 h;

potassium carbonate in N,N-dimethyl-formamide T=110 - 120°C; 5 h;

formaldehyd; toluene-4-sulfonic acid in tetrahydrofuran; water T=100°C; 0.25 h; Microwave irradiation;

potassium carbonate in N,N-dimethyl-formamide T=110°C; 0.5 h;

potassium carbonate in N,N-dimethyl-formamide T=45°C; 18 h;

in water; N,N-dimethyl-formamide

1: 1.) Br2, KBr, 2.) NaOH / 1.) H2O, 6 h, 2.) H2O, 6 h 2: 96 percent / K2CO3 / dimethylformamide / 5 h / 110 - 120 °C View Scheme

2: 96.5 percent / BBr3 / CH2Cl2 / 20 °C 3: 76 percent / K2CO3 / dimethylformamide / 0.5 h / 110 °C View Scheme