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

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.

1. customAnalogously to the literature method [D. Dauzonne, Synthesis, 1990, 66-70]
2. waitat 175° C. for seven hours
3. customremove the organic phase
4. extractionextract the aqueous phase three times with 100 ml of dichloromethane each time
5. dry with materialDry the combined organic extracts over sodium sulphate
6. filtrationfilter
7. concentrationconcentrate under reduced pressure
8. custom11.9 g (85% purity, 64% of theory) of the target compound are obtained

ORD record

ord-1bc3e0e97089499980bd90552e4f63c1

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324222B2