Sodium Cyanide → 2-(2-Methoxy-6-nitrophenyl)acetonitrile

HRID 37868

Reaction equation

HRID 37868 reaction equation
[C-:1]#[N:2].[Na+].Br[CH2:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:7]=1[O:15][CH3:16]>C(O)C>[CH3:16][O:15][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:6]=1[CH2:5][C:1]#[N:2]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 186047Benzene, 2-(bromomethyl)-1-methoxy-3-nitro-

Product 1

HCID 5550182-(2-Methoxy-6-nitrophenyl)acetonitrileYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium cyanide (165 mg, 3.36 mmol) was added to a solution of 2-bromomethyl-1-methoxy-3-nitro-benzene (680 mg, 2.56 mmol) in ethanol (5 mL) and the mixture was heated at reflux overnight. The solvent was removed in vacuo, water (30 mL) was added and the mixture was extracted with dichloromethane (25 mL). The organic phase was washed with water (2×20 mL), brine (20 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The crude compound was purified by column chromatography over silica gel (100-200 mesh) using 8% ethyl acetate in petroleum ether to afford (2-methoxy-6-nitro-phenyl)-acetonitrile (300 mg, 61%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. customThe solvent was removed in vacuo, water (30 mL)
  4. additionwas added
  5. extractionthe mixture was extracted with dichloromethane (25 mL)
  6. washThe organic phase was washed with water (2×20 mL), brine (20 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe crude compound was purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-46ed9c89cd934247a47414a116326a91
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Linked notes

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