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 (9.56 g, 26.4 mmol) and (3,5-difluorophenyl)boronic acid (5.00 g, 31.7 mmol) in toluene (100 mL) and saturated NaHCO3 (80 mL) was bubbled with N2 to degas. Tetrakis(triphenylphosphine)palladium(0) (1.22 g, 1.06 mmol) was added. The reaction mixture was bubbled with N2 for an additional 5 minutes and then heated at 80° C. for 2 hrs. After cooling to room temperature, the mixture was diluted with ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The resulting material was purified on silica gel column, eluting with ethyl acetate/hexane, 0-30%, to give the desired product (8.65 g, 100%). LCMS calculated for C15H11ClFF2NO3 (M+H)+: m/z=326.0; Found: 326.0.

Provenance & Evidence