1-Chloro-2,6-dinitrobenzene → 1,3-Dinitro-2-vinylbenzene

Participants

Reaction Steps

1-Chloro-2,6-dinitrobenzene (1.00 g, 4.94 mmoles, purchased from Lancaster) tris(dibenzylideneacetone)dipalladium (0.113 g, 0.123 mmoles), tri-2-furylphosphine (0.229 g, 0.987 mmoles), copper(I) iodide (0.094 g, 0.494 mmoles), and lithium chloride (0.628 g, 14.8 mmoles) in N,N-dimethylformamide (15 mL) were treated with tributylethenylstannane (2.90 mL, 9.87 mmoles). The reaction mixture was degassed with nitrogen, stirred overnight at room temperature and then heated at 80° C. for 4 hours. The reaction mixture was then diluted with ethyl acetate and washed with water and brine. The organic phase was dried with sodium sulfate, filtered and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 10% ethyl acetate/hexanes) to provide the title compound (0.669 g, 70%). MS (DCI) m/z 194 (M+H)+.

Provenance & Evidence