5-bromo-2,4-dichloropyridine → HCID 90204301, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2,4-dichloropyridine (CAN 849937-96-8, 15 g, 66.1 mmol) in dry THF (300 ml) cooled down to −15° C. under an argon atmosphere was added isopropyl magnesium chloride, lithium chloride complex (53.4 ml, 69.4 mmol) and the mixture was stirred at −15° C. for 1 hour. Then oxetan-3-one (5.24 g, 72.7 mmol) was added neat to the reaction mixture cooled at −15° C., reaction mixture was stirred and let to warm up to room temperature overnight. Reaction was quenched by addition of water and stirred for 5 minutes. Reaction was diluted with ethyl acetate and was transferred into a separatory funnel. The organic phase was extracted with a saturated aqueous solution of ammonium chloride and the organic phase was collected. The aqueous phase was back-extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (10.5 mg, 72%). MS (ESI, m/z): 220.4 (M+H+)

Provenance & Evidence