Triphenylphosphine → (1-Cyanocyclopropyl)-2-bromomethylcyclohexanecarboxamide

Participants

Reaction Steps

(1-Cyanocyclopropyl)-2-hydroxymethyl-cyclohexane-carboxamide was dissolved, along with triphenylphosphine (2.77 g, 10.58 mmol) in tetrahydrofuran (100 mL) (Note—heating was required to effect dissolution). The reaction mixture was cooled carefully in an ice/water bath, ensuring the solution remained homogeneous. N-bromosuccinimide (1.88 g, 10.58 mmol) was added in small portions. Once a clear solution had formed, the cooling bath was removed, and the reaction mixture was permitted to stir overnight. The solvent was evaporated and the residue was purified on a short plug of silica gel (30-60% ethyl acetate/hexane) to give (1-cyanocyclopropyl)-2-bromomethylcyclohexanecarboxamide. MS [ESI, (M+H)+] m/z=285, 287.

Provenance & Evidence