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

HRID 880478

Reaction equation

HRID 880478 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 for 16 h. 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 in vacuo. The crude compound was purified by column chromatography over silica gel (100-200 mesh) using 8% ethyl acetate in petroleum ether to afford 2-(2-methoxy-6-nitro-phenyl)acetonitrile (300 mg, 61%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 h
  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 in vacuo
  9. customThe crude compound was purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-b3f742d668c24a01af5e4f6e95dc25b5
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Linked notes

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