Sodium Carbonate → 2,4-Dibromo-3,5-difluoro-6-(2-fluoro-5-nitrophenyl)pyridine

Participants

Reaction Conditions

Reaction Steps

To a degassed mixture of 2,4,6-tribromo-3,5-difluoropyridine (4.26 g, 12.1 mmol), 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (2.80 g, 10.4 mmol), aqueous sodium carbonate (10 ml of a 2 M solution), and tetrahydrofuran (40 ml) was added tetrakis(triphenylphosphine)palladium(0) (0.67 g). The mixture was then stirred at 55° C. for 48 h under an atmosphere of nitrogen. The reaction mixture was then partitioned between water and ethyl acetate. The organic layer was separated and evaporated, and the residue chromatographed (silica gel, 20-40% CH2Cl2/isohexane) to afford 1.209 g of 2,4-dibromo-3,5-difluoro-6-(2-fluoro-5-nitrophenyl)pyridine as a solid: 1H NMR (400 MHz, CDCl3) δ 7.37 (1H, t, J 8.8 Hz), 8.38 (1H, m), 8.55 (1H, dd, J 2.9, 6.1 Hz).

Provenance & Evidence