Thiophene → 3-Chloro-1-(2-thienyl)-1-propanone

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Reaction Steps

18.1 g of 3-chloropropionyl chloride (142 mmol) are solubilized in dichloromethane (50 mL). The obtained solution is dropwise added to a suspension of AlCl3 (21.6 g; 160 mmoles) in dichloromethane (100 mL). It is left under stirring for 15 minutes at room temperature. A solution of thiophene (12.0 g; 142 mmoles) in dichloromethane (50 mL) is then slowly added while maintaining the temperature at 0° C. At the end the temperature is let to rise to room temperature while stirring for 4 hours. The reaction mixture is poured in a water/ice mixture and then extraction is carried out with diethyl ether. The organic phase is anhydrified with sodium sulphate, filtered and the solvent removed under vacuum. 23.9 g of 3-chloro-1-(thiophen-2-yl)propan-1-one are obtained (yellow oil, yield 99%). Rf=0.75 (ligroin/ethyl acetate 7/3 volume/volume); 1H NMR (CDCl3) δ (ppm): 7.66 (dd, 1H, ArH), 7.60 (dd, 1H, ArH); 7.07 (dd, 1H, ArH), 3.82 (t, 2H, CH2); 3.31 (t, 2H, CH2); 13C NMR (CDCl3) δ (ppm): 189.5, 143.6, 134.4, 132.5, 128.3, 41.8, 38.6; FT-IR (film) νmax: 3093.3, 1657.7, 1413.0, 1240.3, 850.4, 720.7 cm−1.

Provenance & Evidence