2,4-Dichloro-5,7-difluoro-3-methylquinoline → 4-Chloro-5,7-difluoro-3-methyl-2-phenethylquinoline

Participants

Reaction Conditions

Reaction Steps

A screw cap vial was charged with 2,4-dichloro-5,7-difluoro-3-methylquinoline (500 mg, 2.016 mmol), tetrakis(triphenylphosphine)palladium(0) (233 mg, 0.202 mmol), and THF (5.04 mL). The mixture was sparged with N2, then phenethyl-zinc(II) bromide (0.5 M in THF, 4.23 mL, 2.116 mmol) was added and the reaction stirred at 60° C. for 2 h. The reaction was then partitioned between EtOAc and water, and the organic layer washed with brine, dried (MgSO4), and concentrated. The crude material was purified by flash chromatography, eluting with a gradient of 0-15% EtOAc in hexane to give 4-chloro-5,7-difluoro-3-methyl-2-phenethylquinoline. Mass Spectrum (ESI) m/e=318.0 (M+1).

Provenance & Evidence