Hydrochloric Acid → HCID 86665178, compound

Participants

Reaction Steps

To a suspension of sodium hydride (2.87 g, 114 mmol) in THF (15 mL), malononitrile (4.77 mL, 76 mmol) in 2 mL of THF was added dropwise at 0° C. After the gas evolution ceased, 1-iodo-4-(trifluoromethoxy)benzene (5.92 mL, 37.8 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.797 g, 1.135 mmol) were added. This mixture was then heated at reflux under nitrogen overnight. The suspension was cooled to ambient temperature, treated with water, acidified with 1N HCl and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and purified on silica gel (0˜30% ethyl acetate in hexanes) to give 8.2 g of product as a tan solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.48-7.65 (m, 2H) 7.37 (d, J=8.35 Hz, 2H) 5.09 (s, 1H). MS (ESI) m/z 225.1 (M−H)−.

Provenance & Evidence