4-Acetylpyridine → 2-Bromo-1-(pyridin-4-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

To a solution of 18.2 g (150 mmol) 4-acetylpyridine (6-1) in 20 mL 48% HBr was added a 5 mL solution of 7.70 mL bromine in 48% HBr dropwise while heating in a 70° C. oil bath. A thick precipitate formed about midway through the addition, but the reaction was allowed to stir an additional 2 h at 70° C. The reaction was cooled and the precipitate was collected by filtration and washed 3×20 mL with a 1:1 methanol:Et2O solution to provide pure 2-bromo-1-pyridin-4-ylethanone (6-2) after drying under high vacuum: 1H NMR (400 MHz, DMSO-d6) δ 9.0 (d, J=3 Hz, 2H), 8.07 (d, J=3 Hz, 2H), 5.03 (s, 2H).

Provenance & Evidence