Ammonium Chloride → 2-Benzyl-4-chloro-5,7-difluoro-3-methylquinoline

Participants

Reaction Conditions

Reaction Steps

A screw cap vial was sequentially charged with 2,4-dichloro-5,7-difluoro-3-methylquinoline (250 mg, 1.00 mmol), tetrakis(triphenylphosphine)palladium(0) (116 mg, 0.10 mmol), and dry THF (2.52 mL). The mixture was then sparged with N2 prior to the addition of benzylzinc(II) bromide (0.5M in THF, 2.12 mL, 1.06 mmol). The reaction was stirred under N2 at 60° C. for 2 h. The reaction was then cooled to rt, slowly poured over satd aq. ammonium chloride and ice, and extracted with EtOAc. The organic layer was washed with water and brine, dried (MgSO4), and concentrated. The crude product then was triturated with toluene, affording 2-benzyl-4-chloro-5,7-difluoro-3-methylquinoline (155 mg, 0.510 mmol). Mass Spectrum (ESI) m/e=304.0 (M+1).

Provenance & Evidence