Potassium Carbonate → omega-(2-Cyano-4-chlorophenoxy)-2-benzyloxy-acetophenone

HRID 450838Notes

Reaction equation

HRID 450838 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([C:15]#[N:16])[CH:9]=1.Br[CH:18]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20]>CN(C=O)C>[C:15]([C:10]1[CH:9]=[C:8]([Cl:7])[CH:13]=[CH:12][C:11]=1[O:14][CH:18]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20])#[N:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27774205-Chloro-2-hydroxybenzonitrileHCID 20153830omega-Bromo-2-benzyloxy-acetophenone

Product 1

HCID 68535637omega-(2-Cyano-4-chlorophenoxy)-2-benzyloxy-acetophenone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of potassium carbonate (0.06 g, 4.0 mmol), 4-chloro-2-cyanophenol (0.25 g, 1.6 mmol) and ω-bromo-2-benzyloxy-acetophenone (0.49 g, 1.6 mmol) in dry DMF (10 ml) is stirred at room temperature for 20 h. After evaporating the solvent under reduced pressure the residue is taken up in ethyl acetate. The solution is washed with water, dried over sodium sulfate and evaporated under reduced pressure. The residue is purified by silical gel column chromatography to yield the title compound.

Workup

  1. customAfter evaporating the solvent under reduced pressure the residue
  2. washThe solution is washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue is purified by silical gel column chromatography

Sources & evidence

ORD record
ord-d607c6706b354f9e9d4543951294f806
Source dataset
uspto-grants-2013_07
Patent number
US08486996B2

Reaction notes

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