2,6-Dibromopyridine → 2-Bromo-6-(4-bromo-2,6-difluorobenzyl)pyridine

Participants

Reaction Steps

To a solution of 5-bromo-2-(bromomethyl)-1,3-difluorobenzene (from Step B above, 18.5 g, 65.17 mmol) in THF (400 mL) was added 100 mL of Zn/THF solution (5 g Zn/100 mL, 76.46 mmol) at 0° C. The mixture was warmed to room temperature and stirred for 30 minutes. To this reaction was added 2,6-dibromo pyridine (15.44 g, 65.17 mmol) and tetrakis(triphenylphosphine)palladium (7.51 g, 6.51 mmol), and heated to 90° C. for 1 hr. The reaction was monitor by LCMS. After cooling to room temperature, the reaction was quenched with aqueous NH4Cl, and diluted with EtOAc. The organic layer was washed with water (3×), brine (3×), dried over MgSO4, and condensed in vacuo to yield a yellow oil. The crude residue was purified via silica gel chromatography to give the title compound (16 g).

Provenance & Evidence