Hydrochloric Acid → 2-(4-Chlorophenyl)-2-(4-nitrophenyl)acetonitrile

Participants

Reaction Steps

To a solution of 4-chlorobenzylcyanide (5.909 g, 38.979 mmol, 1.1 equip) in THF (100 mL) was added potassium t-butoxide (9.941 g, 88.589 mmol, 2.5 equip) and the solution was stirred for 10 minutes. 4-Fluoronitrobenzene (5.000 g, 35.435 mmol, 1 equip) was added and the reaction mixture stirred at room temperature overnight. The resulting mixture was acidified to pH 7 with 1N HCl, ethyl acetate and water were added, and the layers were separated. The aqueous layer was extracted 1× with ethyl acetate, and the organic layers were combined, dried (Na2SO4), and concentrated. The residue was purified by MPLC using an ethyl acetate-heptane gradient to yield 2-(4-chlorophenyl)-2-(4-nitrophenyl)acetonitrile as an orange-yellow solid.

Provenance & Evidence