4-Ethylbenzaldehyde → 1-[(Z)-2-Chloro-2-nitrovinyl]-4-ethylbenzene

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Reaction Steps

Analogously to the literature method [D. Dauzonne, Synthesis, 1990, 66-70], stir a mixture of 10.0 g (74.5 mmol) of 4-ethylbenzaldehyde, 6.8 ml (13.7 g, 97.6 mmol) of bromonitromethane, 54.7 g (670.7 mmol) of dimethylammonium chloride and 0.6 g (11.2 mmol) of potassium fluoride in 150 ml of xylene on a water separator at 160° C. for 15 hours and then at 175° C. for seven hours. After adding 25 ml of water and 100 ml of dichloromethane, remove the organic phase and extract the aqueous phase three times with 100 ml of dichloromethane each time. Dry the combined organic extracts over sodium sulphate, filter and concentrate under reduced pressure. Chromatograph the residue on silica gel (eluent: cyclohexane/dichloromethane 1:1). 11.9 g (85% purity, 64% of theory) of the target compound are obtained.

Provenance & Evidence