4-Fluoroiodobenzene → HCID 178476783, compound

Participants

Reaction Steps

To a degassed mixture of 4-fluoro-1-iodo-benzene (25.0 g, 112.6 mmol), anilinium hypophosphite (21.5 g, 135.1 mmol) and 3-aminopropyl triethoxysilane (24.9 g, 135.1 mmol) in anhydrous acetonitrile (750 mL) were added palladium acetate (560 mg, 2.48 mmol) and 1,3-bis(diphenylphosphino)propane (1.02 g, 2.48 mmol). The mixture was heated under reflux overnight, then cooled down to room temperature, and the volatiles were removed in vacuo. The residue was diluted with ethyl acetate and hydrochloric acid (1 M) and partitioned. The aqueous layer was further extracted with ethyl acetate and the combined extracts were washed with aqueous sodium hydrogen carbonate and brine. The volatiles were removed in vacuo, then the residue was purified by column chromatography using 50 to 100% ethyl acetate in petroleum ether, affording compound AZ2 (10.1 g) as a dark orange oil in 48% yield.

Provenance & Evidence