sodium carbonate; potassium hexacyanoferrate(III); palladium diacetate in N,N-dimethyl acetamide T=120°C; 10 h;

sodium carbonate; palladium diacetate in N,N-dimethyl acetamide T=120°C; 10 h;

sodium carbonate; palladium diacetate in dimethyl amine T=20 - 120°C; 22 h;

sulfuric acid in methanol; ethyl acetate

in diethyl ether T=25°C;

1: CH2Cl2 / 14 h / Ambient temperature 2: 70 percent / thionyl chloride / benzene; CH2Cl2 / 1.) reflux, 2.) room temperature, 2.5 h 3: 1.) n-butyllithium, 3.) ethanol / 1.) pentane/diethyl ether, -78 deg C, 0.5 h, 2.) pentane/diethyl ether, room temperature, 45 min, 3.) pentane/diethyl ether, room temperature, 2 h 4: 1.) 4.5 N HCl / 1.) reflux, 15 h View Scheme

1: 70 percent / thionyl chloride / benzene; CH2Cl2 / 1.) reflux, 2.) room temperature, 2.5 h 2: 1.) n-butyllithium, 3.) ethanol / 1.) pentane/diethyl ether, -78 deg C, 0.5 h, 2.) pentane/diethyl ether, room temperature, 45 min, 3.) pentane/diethyl ether, room temperature, 2 h 3: 1.) 4.5 N HCl / 1.) reflux, 15 h View Scheme

1: thionyl chloride / 1 h / 100 °C 2: CH2Cl2 / 14 h / Ambient temperature 3: 70 percent / thionyl chloride / benzene; CH2Cl2 / 1.) reflux, 2.) room temperature, 2.5 h 4: 1.) n-butyllithium, 3.) ethanol / 1.) pentane/diethyl ether, -78 deg C, 0.5 h, 2.) pentane/diethyl ether, room temperature, 45 min, 3.) pentane/diethyl ether, room temperature, 2 h 5: 1.) 4.5 N HCl / 1.) reflux, 15 h View Scheme

1: 1.) n-butyllithium, 3.) ethanol / 1.) pentane/diethyl ether, -78 deg C, 0.5 h, 2.) pentane/diethyl ether, room temperature, 45 min, 3.) pentane/diethyl ether, room temperature, 2 h 2: 1.) 4.5 N HCl / 1.) reflux, 15 h View Scheme

hydrogenchloride 1.) reflux, 15 h; Yield given. Multistep reaction;