copper; potassium carbonate in N,N-dimethyl-formamide T=160°C; Ullmann reaction;

potassium hydroxide; copper in water 14 h; Heating;

copper; potassium carbonate in N,N-dimethyl-formamide 12 h; Heating;

1: LiAlH4 / diethyl ether; tetrahydrofuran / 4 h / Heating 2: thionyl chloride / toluene / 1 h / 80 °C 3: ethanol; H2O / 12 h / Heating 4: aq. KOH / ethanol / 3 h / Heating 5: polyphosphoric acid / toluene / 4 h / Heating 6: 62 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 7: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 8: conc. HCl / ethanol / 1 h / Heating View Scheme

1: LiAlH4 / diethyl ether; tetrahydrofuran / 4 h / Heating 2: thionyl chloride / toluene / 1 h / 80 °C 3: ethanol; H2O / 12 h / Heating 4: aq. KOH / ethanol / 3 h / Heating 5: polyphosphoric acid / toluene / 4 h / Heating 6: 57 percent / sodium, liq. NH3, ferric nitrate / tetrahydrofuran / 1 h / -30 °C 7: 82 percent / pyridine hydrochloride / 0.5 h / 210 °C 8: 62 percent / K2CO3 / acetone; dimethylformamide / 18 h / Heating 9: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 10: conc. HCl / ethanol / 1 h / Heating View Scheme

1: LiAlH4 / diethyl ether; tetrahydrofuran / 4 h / Heating 2: thionyl chloride / toluene / 1 h / 80 °C View Scheme

sodium bis(2-methoxyethoxy)aluminium dihydride in benzene

1: LiAlH4 / diethyl ether; tetrahydrofuran / 4 h / Heating 2: thionyl chloride / toluene / 1 h / 80 °C 3: ethanol; H2O / 12 h / Heating View Scheme

1: LiAlH4 / diethyl ether; tetrahydrofuran / 4 h / Heating 2: thionyl chloride / toluene / 1 h / 80 °C 3: ethanol; H2O / 12 h / Heating 4: aq. KOH / ethanol / 3 h / Heating View Scheme