Ethyl bromoacetate → HCID 68725817, compound

HRID 493212Notes

Reaction equation

HRID 493212 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([OH:10])=[C:4]([CH:11]([OH:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(#N)C>[CH2:30]([O:29][C:27](=[O:28])[CH2:26][O:10][C:5]1[CH:6]=[C:7]([O:8][CH3:9])[C:2]([Cl:1])=[CH:3][C:4]=1[CH:11]([OH:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH3:31]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 68724734HCID 68724734, compound

Product 1

HCID 68725817HCID 68725817, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the above prepared 4-chloro-2-(hydroxy-phenyl-methyl)-5-methoxy-phenol (1.39 g, 5.25 mmol) in 15 mL acetonitrile were successively added Cs2CO3 (2.22 g, 1.3 eq.) and ethyl bromoacetate (0.67 mL 1.15 eq.) and the mixture vigorously stirred at ambient temperature over night. Pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents left 1.91 g of the title compound as off-white gum, 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 sodium sulfate, and evaporation of the solvents
  5. waitleft 1.91 g of the title compound as off-white gum

Sources & evidence

ORD record
ord-6f93b90dcb8a442db948b9581e9c7c95
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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