Picolinic acid → Diethyl (3-fluorophenyl)propanedioate

Participants

Reaction Steps

A round bottom flask was charged with copper (I) iodide (571 mg, 3.0 mmol), 2-picolinic acid (739 mg, 6.0 mmol), and Cs2CO3 (58.6 g, 180 mmol). The flask was evacuated and re-filled with argon (3 times). 1,4-dioxane (60 mL), diethylmalonate (18.2 mL, 120 mmol), and 3-fluoroiodobenzene (7.05 mL, 60 mmol) were then added in sequence. The resulting yellow suspension was stirred at room temperature overnight. To the mixture was added sat aqueous NH4Cl and the mixture was extracted with EtOAc (3×). The organic phase was washed once with water. The organic phase was dried (Na2SO4), filtered, and concentrated to yield the crude title compound as a colorless liquid, which was used without further purification.

Provenance & Evidence