Acetonitrile → 3-(4-Chloromethyl-phenyl)-propionitrile

Participants

Reaction Conditions

Reaction Steps

Acetonitrile (0.30 mL, 5.7 mmol) was added to a solution of n-butyllithium (2.4 m in hexanes, 1.96 mL, 4.7 mmol) in dry THF (5 mL) at −78° C. and stirred for 45 min. solution of α,α′-dichloro-p-xylene (2.485 g, 14.2 mmol) in dry THF at −78° C. was added to give a yellow, cloudy solution. The mixture was stirred at −78° C. for an additional hour and quenched with saturated aqueous NaCl (30 mL) before warming to room temperature. The mixture was, extracted with CH2Cl2 (3×200 mL). The combined organic extracts were dried over MgSO4 and concentrated to a white solid (2.45 g). The product was purified by column chromatography on silica gel (10:1—EtOAc:Hex) to give the desired nitrile (1.49 g, 60%) as a light yellow syrup. 1H NMR (300 MHz, CDCl3) δ 7.37 (d, 2H, J=8.1 Hz), 7.24 (d, 2H, J=8.1 Hz), 4.58 (s, 2H), 2.96 (t, 2H, J=7.4 Hz), 2.62 (t, 2H, J=7.4 Hz).

Provenance & Evidence