Bromine → 5-Bromo-3-fluoro-1,2-dihydropyridin-2-one

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-fluoro-2-hydroxypyridine (1 g, 8.8 mmol) in dry DMF (11 mL) was cooled in an ice bath. Bromine (1.55 g, 9.7 mmol) was added dropwise over a period of 10 min and the reaction mixture stirred at 0° C. for 1 h then allowed to warm to room temperature and stirred for an additional 2 h. The reaction was quenched with water. The aqueous was extracted with DCM (×4) and the combined organics dried (MgSO4) and concentrated in vacuo. Purification by column chromatography (gradient: 20-100% EtOAc in petroleum ether 40-60) yielded the target compound as a pale yellow solid.

Provenance & Evidence