2,6-Dibromopyridine → 2-Bromo-6-tert-butylpyridine

Participants

Reaction Steps

To potassium tert-butoxide (1.0M in tert butanol, 100 ml, 100 mmol) was added 2,6-dibromopyridine (15.87 g, 67 mmol), and the resulting mixture heated at reflux for 3.5 hours. The mixture was evaporated and the residue quenched by the addition of water (150 ml). The mixture was extracted with ethyl acetate (3×80 ml) and the combined organic layers washed with brine (100 ml), dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica eluting with 2% Et2O in iso-hexanes to give the title compound (9.9 g, 69%) as a clear oil.

Provenance & Evidence