Sodium Cyanide → (2-Methoxy-5-nitrophenyl)acetonitrile

HRID 495454Notes

Reaction equation

HRID 495454 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

HCID 8929Sodium CyanideHCID 775162-(Bromomethyl)-1-methoxy-4-nitrobenzene

Product 1

HCID 12701835(2-Methoxy-5-nitrophenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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 water) 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.

Workup

  1. additionAfter the addition
  2. stirringthe reaction was stirred at 70° C. for 90 min
  3. customThe inorganic solid, which separated
  4. temperatureon cooling
  5. customwas collected
  6. washwashed well with CH3CN
  7. filtrationThe CH3CN filtrate was filtered again
  8. customgiving further inorganic solid
  9. washagain washed with CH3CN
  10. customThe final CH3CN filtrate was evaporated
  11. customgiving a red-brown solid
  12. customThis solid was triturated with CH2Cl2 until the washings
  13. customEvaporation of the CH2Cl2 filtrate

Sources & evidence

ORD record
ord-e7277dcabd3448eeb64dc995d5a53cc2
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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