Ethyl bromoacetate → Ethyl (4-cyanophenoxy)acetate

HRID 2181181Notes

Reaction equation

HRID 2181181 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 130194-Cyanophenol

Product 1

HCID 207426Ethyl (4-cyanophenoxy)acetateYield 95.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 22.16 g (0.186 mol) of 4-cyanophenol, 32.07 g (0.192 mol) of ethyl bromoacetate, 27.6 g (0.199 mol) of K2CO3 and acetone (250 ml) is stirred at room temperature for 12 hours. After filtration, the solvent is evaporated off under vacuum and the residue is partitioned between an organic phase (ethyl acetate) and an aqueous phase (water). The organic layer is dried (MgSO4) and concentrated under vacuum to give 36.42 g (95%) of ethyl 4-cyanophenoxyacetate (white solid, melting point: 49-50° C.).

Workup

  1. filtrationAfter filtration
  2. customthe solvent is evaporated off under vacuum
  3. customthe residue is partitioned between an organic phase (ethyl acetate)
  4. dry with materialThe organic layer is dried (MgSO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5525e8750798467d80d46824b1d3c1f0
Source dataset
uspto-grants-2005_05
Patent number
US06890955B2

Reaction notes

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