1-(3-Bromophenyl)-2,5-dihydro-1H-pyrrole → 2,5-Dihydro-1-[3-(phenylmethyl)phenyl]-1H-pyrrole

Participants

Reaction Steps

To a mixture of 6.6 g of 1-(3-bromophenyl)-2,5-dihydropyrrole, 800 mg of 1,3-bis(diphenylphosphino)propanenickel (II) chloride and 40 ml of tetrahydrofuran was added dropwise 22 ml of a 2.0 M tetrahydrofuran solution of benzyl magnesium chloride, followed by stirring overnight as it was. The reaction mixture was separated with a saturated aqueous ammonium chloride solution-ethyl acetate, and the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and then evaporated. The residue was purified by silica gel column chromatography with 1% ethyl acetate/hexane, to give 2.1 g of the title compound.

Provenance & Evidence