N-bromobutanimide → HCID 18986082, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-2-methylpyridine (2.0 g, 11.63 mmol), NBS (2.69 g, 15.11 mmol), and diphenylperoxyanhydride (0.282 g, 1.163 mmol) in carbon tetrachloride (50 mL) was heated to 100° C. overnight. Cooled to RT, diluted with saturated NaHCO3, and extracted with ethyl acetate (3×). The combined organic extracts were washed with saturated NaCl (2×), dried over Na2SO4, filtered, and concentrated. The residue was purified via silica gel chromatography (ISCO, 120 g silica, 60 mL/min, 0-80% EtOAc/Hexanes over 45 min) to afford 4-bromo-2-(bromomethyl)pyridine (1.05 g, 36%). MS (m/z) 251.9.

Provenance & Evidence