Sodium Cyanide → (2-Methoxy-5-nitrophenyl)acetonitrile
Reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[O:12][CH3:13].[C-:14]#[N:15].[Na+]>CCO>[CH3:13][O:12][C:4]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[CH2:2][C:14]#[N:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Bromomethyl-1-methoxy-4-nitro-benzene (25 g) was dissolved in warm EtOH (45 mL) and stirred while slowly adding a solution of NaCN (6.0 g in 12 mL H2O) at 70° C. After the addition was complete, the reaction was stirred at 70° C. for 90 min. The inorganic solid, which separated on cooling, was collected and washed well with CH3CN. The CH3CN filtrate was filtered again giving further inorganic solid, and again washed with CH3CN. The final CH3CN filtrate was evaporated giving a red-brown solid. This solid was triturated with CH2Cl2 until the washings were colorless. Evaporation of the CH2Cl2 filtrate gave (2-methoxy-5-nitrophenyl)-acetonitrile as a red-brown solid, which was used without further purification.