Benzyl Bromide → 1-Benzylcyclopropanecarbonitrile

Participants

Reaction Steps

A solution of cyclopropyl cyanide (3.0 mL, 40 mmol) in 20 mL THF was dropwise added to a stirred, freshly prepared, mixture of lithium diisopropylamide (40 mmol) in THF (100 mL) at −78° C. After 30 min, a solution of benzyl bromide 7.8 mL, 60 mmol) in THF (20 mL) was dropwise added. The resulting mixture was warmed slowly over several hrs and stirred at rt 48 hr. The reaction was quenched (250 mL saturated NH4Cl), extracted with ether (3×100 mL) and the combined organic extracts were dried (MgSO4), filtered and concentrated to afford a yellow oil.

Provenance & Evidence