o-Iodonitrobenzene → 2-(2-nitrophenyl)thiophene

Participants

Reaction Steps

Bis(triphenylphosphine)palladium(II) chloride (350 mg) and 2-(tributylstannyl)thiophene (57 g, 0.15 mol) were added to a solution of 1-iodo-2-nitrobenzene (35 g, 0.14 mol) in 500 ml of N,N-dimethylformamide. This mixture was heated for 16 h to 100° C. After concentration in vacuo, the residue was taken up in diethyl ether, washed with water and brine, dried over magnesium sulfate and evaporated. The remaining oil was purified by silica gel chromatography using ethyl acetate and hexane as eluents, yielding 23 g of 2-(2-nitro-phenyl)-thiophene.

Provenance & Evidence