Ethyl bromoacetate → (2-Isobutyryl-5-methoxy-phenoxy)-acetic acid ethyl ester

HRID 493189Notes

Reaction equation

HRID 493189 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:14])[CH:11]([CH3:13])[CH3:12].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(#N)C>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][O:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:14])[CH:11]([CH3:12])[CH3:13])[CH3:27]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 687238621-(2-Hydroxy-4-methoxy-phenyl)-2-methyl-propan-1-one

Product 1

HCID 68725425(2-Isobutyryl-5-methoxy-phenoxy)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the above prepared 1-(2-hydroxy-4-methoxy-phenyl)-2-methyl-propan-1-one (5.43 g, 28 mmol) in 56 mL acetonitrile were successively added Cs2CO3 (10.9 g, 1.2 eq.) and ethyl bromoacetate (3.25 mL, 1.05 eq.) and the mixture vigorously stirred at ambient temperature for 2.5 h. Pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents left 8.01 g of the title product as light yellow oil, sufficiently pure to be used for the next step.

Workup

  1. additionPouring
  2. extractionice/NH4Cl, twofold extraction with AcOEt
  3. washwashing with water
  4. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  5. waitleft 8.01 g of the title product as light yellow oil

Sources & evidence

ORD record
ord-74914955efa14dfba5c42ac236010ebf
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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