Hydrochloric Acid → 3-(4-Chlorophenyl)prop-2-enal

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-chloro-4-iodobenzene (2 g, 8.39 mmol) in DMF (30 mL) were added acrolein diethyl acetal (3.84 mL, 8.39 mmol), n-Bu4NOAc (5.06 g, 16.8 mmol), K2CO3 (1.74 g, 12.6 mmol), KCl (0.63 g, 8.39 mmol) and Pd(OAc)2 (0.056 g, 0.25 mmol). The mixture was stirred for 1.5 hour at 90° C. After cooling, 2 N HCl was slowly added and the reaction mixture was stirred at room temperature for 10 minutes. Subsequently, it was diluted with ether (200 mL) and washed with water (200 mL). The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (n-hexane/ethyl acetate mixture in a volume ratio 8:2) to give intermediate 5d (74% yield) which was characterised as follows:

Provenance & Evidence