Nitrogen → 3-Acetyl-5-bromopyridine

Participants

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a suspension of 3,5-dibromopyridine (2.39 g, 10.00 mmol) in ether (70.0 mL) was treated at −78° C. with n-BuLi (4.0 mL of a 2.5M solution in hexane, 10.00 mmol). The reaction mixture was stirred for 30 min before N,N-dimethylacetaminde (1.50 mL, 16.13 mmol) was added and the solution was then allowed to warm to rt over 1 h. Sat. aq. NH4Cl was then added and the aq. layer was extracted with Et2O (2×50 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (10:1 hept-EA) gave the title compound as a white solid. TLC: rf (19:1 CH2Cl2-MeOH)=0.57. LC-MS-conditions 02: tR=0.80 min.

Provenance & Evidence