Dimethylformamide → [2-Chloro-5-(methoxymethoxy)phenyl]acetonitrile

HRID 420550Notes

Reaction equation

HRID 420550 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9]COC)=[CH:4][C:3]=1[CH3:13].Br[N:15]1C(=O)CC[C:16]1=O.[C-]#N.[Na+].CN(C)[CH:27]=[O:28]>C(Cl)(Cl)(Cl)Cl.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:28][CH3:27])=[CH:4][C:3]=1[CH2:13][C:16]#[N:15]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 67184N-bromobutanimideHCID 22467254HCID 22467254, compound

Product 1

HCID 57966326[2-Chloro-5-(methoxymethoxy)phenyl]acetonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-chloro-5-(methoxyethoxy)toluene (5.00 g; 26.8 mmol), N-bromosuccinimide (4.77 g; 26.8 mmol) and 2,2-azobis(isobutyronitrile) (0.09 g; 0.53 mmol) in carbon tetrachloride (25 ml) was refluxed for 2 hours. After air cooling and filtration the precipitate, the filtrate was condensed under reduced pressure. To the residue were added sodium cyanide (2.77 g; 80.4 mol) and anhydrous N,N-dimethylformamide (30 ml). The mixture was stirred at room temperature for 2 hours. Water and ethyl acetate were added to the reaction solution and extracted. The organic layer was washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=6:1→4:1) to give [2-chloro-5-(methoxymethoxy)phenyl]acetonitrile as colorless oil (2.64 g; 47%).

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter air cooling
  3. filtrationfiltration the precipitate
  4. customcondensed under reduced pressure
  5. extractionextracted
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=6:1→4:1)

Sources & evidence

ORD record
ord-eccd55db5c514dd491397726262db87f
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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