1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / Inert atmosphere 2.1: 0.5 h / Inert atmosphere 3.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; zinc(II) chloride; zinc / tetrahydrofuran / 24 h / 60 °C / Inert atmosphere 4.1: potassium hydroxide / aacetone / 2 h / Reflux; Inert atmosphere 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 2 h / Inert atmosphere; Reflux 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere 6.2: 20 °C View Scheme

1: oxalyl chloride / CH2Cl2 / 1.5 h / Heating 2: 891 mg / Et3N / CH2Cl2 / 0.83 h / 20 °C 3: 96 percent / NaH / dimethylformamide / 1.5 h / 20 °C 4: 94 percent / Ag2CO3 / Pd(OAc)2; P(o-Tol)3 / dimethylformamide / 0.33 h / Heating View Scheme

1: benzyl alcohol; copper-powder 2: thionyl chloride 3: toluene; ethyl acetate 4: acetic acid; aqueous hydrochloric acid / Erhitzen des Reaktionsprodukts mit Benzoesaeure-anhydrid und Natriumbenzoat auf 190grad View Scheme

1: SOCl2 2: 83 percent / Et3N / tetrahydrofuran / 12 h / Ambient temperature 3: 89 percent / CuI, Et3N / PdCl2(PPh3)2 / 6 h / Ambient temperature 4: 95 percent / K2CO3 / methanol / 0.5 h / Ambient temperature 5: 61 percent / n-Bu3SnH, AIBN / benzene / 5 h / Heating View Scheme