1-Iodo-3-nitrobenzene → 1-{4-[(6-Bromohexyl)oxy]but-1-ynyl}-3-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-iodo-3-nitrobenzene (3 g), 6-bromohexyl but-3-ynyl ether (3 g), bis(triphenylphosphine)palladium (II) chloride (0.421 g), copper (I) iodide (0.114 g) in DMF (10 ml) and diisopropylethylamine (4 ml) was stirred under nitrogen at 20° C. for 5 h. The mixture was concentrated under reduced pressure and the residue was diluted in EtOAc and washed with 2M HCl, NaHCO3, brine and dried (MgSO4). The solvent was removed by evaporation and the residue was chromatographed on a Biotage column eluting with ether:petroleum ether(40–60° C.) (1:9) to give the title compound (4.12 g). LCMS RT=4.14 min

Provenance & Evidence