Sodium Cyanide → Methyl 3-(cyanomethyl)benzoate

Participants

Reaction Steps

Methyl 3-(bromomethyl)benzoate (8.5 g, 37 mmol) and sodium cyanide (1,8 g, 37 mmol) were stirred at room temperature in DMF (40 mL) overnight. The mixture was diluted with EtOAc and extracted several times with water containing a small amount of brine, then brine, dried (MgSO4), and solvent removed in vacuo. The crude product (6.8 g, yellow oil) was sufficiently pure to be used in the next step without purification. IR(neat): cm-1 2249, 1722. 1H-NMR(300 MHz, CDCl3): 8.03-8.01 (m, 2H), 7.57-7.46 (m, 2H), 3.94 (s, 3H), 3.82 (s, 2H).

Provenance & Evidence