Thiophene → 4-(Thiophen-2-yl)benzaldehyde

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

3.7 g (20 mmol) of 4-bromobenzaldehyde, 9.5 ml (120 mmol) of thiophene, 2.94 g (30 mmol) of potassium acetate and 1.16 g (1 mmol) of tetrakis(triphenylphosphine)-palladium (Fluka, Buchs, Switzerland) in 50 ml of dimethylacetamide are placed in a pressure reactor and stirred at 150° C. under nitrogen for 16 hours. The reaction mixture is concentrated by evaporation; the residue is taken up in water and extracted three times with methylene chloride. After removal of the solvent, the residue is chromatographed on silica gel (hexanelethyl acetate 4:1). The title compound is obtained in the form of a yellow solid. TLC: Rf=0.36 (hexane/ethyl acetate 4:1). HPLC20-100: tRet=15.26. 1H-NMR (CD3OD; 200 MHz): 9.98/s (1H); 7.93 and 7.85/each d, J=9.5 (2×2H); 7.60/d, J=2.5 (1H); (1H); 7.17/d×d, J=2.5 and 5 (1H).

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