Hexane → HCID 67294665, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium in hexane(2.50 M, 9.02 mL, 22.5 mmol) was added dropwise to a solution of 1,3-difluorobenzene (2.03 mL, 20.6 mmol) in anhydrous tetrahydrofuran (30 mL) at −78° C. and the resulting solution was stirred at the same temperature for 30 min, then warmed to −50° C. and zinc dichloride in tetrahydrofuran 0.50 M, 45.1 mL, 22.5 mmol) was added slowly. After 20 min, 5-bromo-2-iodopyridine (7.0 g, 25 mmol) in tetrahydrofuran (20 mL) and tetrakis(triphenylphosphine)palladium(0) (1.19 g, 1.03 mmol) were added sequentially. The vessel was partially evacuated and back filled with nitrogen three times, sparged with a gentle stream of nitrogen for 5 minutes, and warmed to ambient temperature. The bright yellow, translucent reaction solution was stirred for 15 minutes at ambient temperature, then heated at 40° C. for 16 hr. The reaction mixture as then cooled to ambient temperature, concentrated, and purified by flash chromatography (90 g silica gel, 0 to 10% ethyl acetate in hexanes) to afford the title compound (14 g) as a tan solid.

Provenance & Evidence