Water → 1-Chloro-4-methoxy-5-nitro-2-vinylbenzene

Participants

Reaction Steps

A mixture of 1-bromo-2-chloro-5-fluoro-4-nitrobenzene (13.0 g, 49.24 mmol), PdCl2(dppf).DCM (0.804 g, 0.98 mmol), potassium ethenyl(trifluoro)borate (7.88 g, 59.09 mmol) and triethylamine (6.87 mL, 49.24 mmol) in n-propanol (130 mL) was heated to reflux for 4 hours. The mixture was allowed to cool to room temperature and poured into water (500 mL). The mixture was extracted with DCM (2×300 mL) then the combined organic extracts were dried (Na2SO4) and the solvent removed under reduced pressure. The residue was purified by column chromatography on neutral silica gel using 1-2% ethyl acetate in hexane to give the title compound (7.8 g, 75%) as a white solid.

Provenance & Evidence