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

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.

1. temperaturethe resulting mixture heated
2. temperatureat reflux for 3.5 hours
3. customThe mixture was evaporated
4. customthe residue quenched by the addition of water (150 ml)
5. extractionThe mixture was extracted with ethyl acetate (3×80 ml)
6. washthe combined organic layers washed with brine (100 ml)
7. dry with materialdried (Na2SO4)
8. customevaporated
9. customThe residue was purified by column chromatography on silica eluting with 2% Et2O in iso-hexanes

ORD record

ord-0531fcf1c9944f65916d021d0554aa62

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07285563B2