Ethyl bromoacetate → Ethyl (4-cyanophenoxy)acetate

HRID 1167291Notes

Reaction equation

HRID 1167291 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>CN(C)C=O.C(OCC)(=O)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:3][CH:4]=1)#[N:7]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 130194-Cyanophenol

Product 1

HCID 207426Ethyl (4-cyanophenoxy)acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-hydroxy-benzonitrile (1 g, 8.395 mmol) in dimethylformamide (10 mL) were added potassium carbonate (2.321 g, 16.79 mmol) and ethyl bromoacetate (1.117 mL, 10.07 mmol), respectively. The reaction mixture was stirred at room temperature for 23 h. It was taken in ethyl acetate and diethyl ether (1:1 ratio), and the solid was filtered off. The filtrate was washed with water, brine and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo to afford ethyl (4-cyano-phenoxy)-acetate. It was used without further purification.

Workup

  1. filtrationdiethyl ether (1:1 ratio), and the solid was filtered off
  2. washThe filtrate was washed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe solid was then filtered off
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c98bde37439346b89017b6688a629295
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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