Sodium Azide → 2-(Azidomethyl)benzonitrile

Participants

Reaction Steps

A mixture of 2-bromomethyl-benzonitrile (300 mg, 1.53 mmol) and sodium azide (129 mg, 1.99 mmol) in acetone was stirred overnight at rt. The solvent was removed, and the resulting residue was chromatographered using hexane/ethyl acetate (6:1) to give the title compound (212 mg, 88%). MS (DCI/NH3) m/z 176 (M+18)+. 1H NMR. (400 MHz, DMSO-d6) δ ppm 4.69 (s, 2 H) 7.58 (td, J=7.67, 1.23 Hz, 1 H) 7.66 (d, J=7.67 Hz, 1 H) 7.76 (td, J=7.67, 1.23 Hz, 1 H) 7.91 (dd, J=7.67, 1.53 Hz, 1 H).

Provenance & Evidence