Nitrogen → 1-(4-Chloro-3',5'-difluoro-5-methyl-6-nitrobiphenyl-2-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

A biphasic solution of 6-acetyl-4-chloro-3-methyl-2-nitrophenyl trifluoromethanesulfonate (9.6 g, 26 mmol) and (3,5-difluorophenyl)boronic acid (5.0 g, 32 mmol) in toluene (100 mL) and saturated sodium bicarbonate in water (100 mL) was bubbled with N2 to degas. After tetrakis(triphenylphosphine)palladium(0) (1.22 g, 1.06 mmol) was added, the mixture was bubbled with N2 for 5 min. more and heated at 80° C. for 2 hours. The mixture was cooled to room temperature and diluted with ethyl acetate. The layers were separated and the aq. layer was extracted with more ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel column, eluting with 0-30% ethyl acetate in hexane, to give the desired product. LCMS calculated for C15H11ClF2NO3 (M+H)+: m/z=326.0. found: 326.0.

Provenance & Evidence