Cesium carbonate → 4-Chloro-1-ethenyl-2-nitrobenzene

Participants

Reaction Steps

Bromo-4-chloro-2-nitrobenzene (3 g, 12.69 mmol), potassium vinyltrifluoroborate (2.039 g, 15.23 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.857 g, 2.54 mmol), cesium carbonate (8.27 g, 25.4 mmol) and THF (50 mL) were heated in an 80° C. oil bath overnight. Volatiles were removed under reduced pressure. The pot residue was worked up with brine, extracted with ethyl acetate, dried over Na2SO4, filtered and evaporated to afford a dark mixture. The resulting crude mixture was purified by flash chromatography (SiO2, Biotage 65i cartridge). The column was eluted by an EtOAc/hexane mixture (0% to 10%). Related fractions were pooled and evaporated to afford a yellow solid as the titled compound. 1H-NMR (CDCl3, 600 MHz) δ 7.94 (d, J=2.4 Hz, 1H), 7.60-7.54 (m, 2H), 7.12 (dd, J=17.4, 10.8 Hz, 1H), 5.75 (d, J=16.8 Hz, 1H), 5.52 (d, J=10.8 Hz).

Provenance & Evidence