Ethyl bromoacetate → (2-Acetyl-4-chloro-5-methoxy-phenoxy)-acetic acid ethyl ester

HRID 493218Notes

Reaction equation

HRID 493218 reaction equation
[Cl:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>C(#N)C>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][O:11][C:5]1[CH:4]=[C:3]([O:12][CH3:13])[C:2]([Cl:1])=[CH:7][C:6]=1[C:8](=[O:10])[CH3:9])[CH3:26]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 150846361-(5-Chloro-2-hydroxy-4-methoxyphenyl)ethanone

Product 1

HCID 68726576(2-Acetyl-4-chloro-5-methoxy-phenoxy)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the above prepared 1-(5-chloro-2-hydroxy-4-methoxy-phenyl)-ethanone (4.22 g, 21.0 mmol) in 50 mL of acetonitrile were successively added Cs2CO3 (8.22 g, 1.2 eq.) and ethyl bromoacetate (2.44 mL, 1.05 eq.) and the mixture vigorously stirred at ambient temperature for 2 h. Pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water, drying over magnesium sulfate, and evaporation of the solvents left 6.05 g of the title compound as off-white solid, used directly for the next step.

Workup

  1. additionPouring
  2. extractionice/NH4Cl, twofold extraction with AcOEt
  3. washwashing with water
  4. dry with materialdrying over magnesium sulfate, and evaporation of the solvents
  5. waitleft 6.05 g of the title compound as off-white solid

Sources & evidence

ORD record
ord-5ac591c1e36a4c86ad197adda4c58dc0
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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