Hydrochloric Acid → 1-Propanone, 3-chloro-1-(5-nitrobenzo[b]thien-3-yl)-

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Reaction Steps

A solution of 1 g (5.58×10−3 moles) of 5-nitrobenzo[b]thiophene and 0.65 ml (6.64×10−3 moles) of 2-chloropropionyl chloride dissolved in 40 ml of dry chloroform was added dropwise over 650 mg of aluminum trichloride, dissolved in 20 ml dry chloroform under a nitrogen atmosphere. The mixture was left to react for 24 hours at room temperature and an additional amount of 650 mg of aluminum trichloride and 0.65 ml of 2-chloropropionyl chloride was added. After 48 hours reaction 100 ml of HCl 1.5N were added, followed by decantation and the organic phase was subsequently washed with a dilute solution of NaHCO3, with H2O and with a saturated solution of NaCl. It was dried with Na2SO4, the solvent was removed and it was purified in a silica column using hexane/toluene (25:75) as mobile phase. Yield: 30%.

Provenance & Evidence