Diethyl Ether → HCID 54156575, compound

HRID 1004379Notes

Reaction equation

HRID 1004379 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[N:12][O:13][CH3:14])[C:10]#[N:11].[Cl:15][C:16]1[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)C>CN(C)C=O>[Cl:15][C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=1)[O:22][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[N:12][O:13][CH3:14])[C:10]#[N:11]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 79333-ChlorophenolHCID 11430Potassium CarbonateHCID 54565929HCID 54565929, compound

Product 1

HCID 54156575HCID 54156575, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromomethyl-α-methoxyiminophenylacetonitrile (5.0 g, 20 mmol) and 3-chlorophenol (3.0 g, 23 mmol) were dissolved in N,N-dimethylformamide (25 ml), and the mixture was stirred at room temperature for 2 hours in the presence of potassium carbonate (3.3 g, 24 mmol). After completion of the reaction, diethyl ether (ca. 100 ml) was added to the reaction mixture, and the mixture was washed successively with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane) and crystallized from diethyl ether/n-hexane to give 2-(3-chlorophenoxymethyl)-α-methoxyiminophenylacetonitrile (3.7 g, 62%) as colorless crystals.

Workup

  1. additionwas added to the reaction mixture
  2. washthe mixture was washed successively with water and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane)
  6. customcrystallized from diethyl ether/n-hexane

Sources & evidence

ORD record
ord-178cfb5e61224993a3a4c33cffdaf6d2
Source dataset
uspto-grants-2000_04
Patent number
US06048885

Reaction notes

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