Ethyl bromoacetate → HCID 68727506, compound

HRID 493203Notes

Reaction equation

HRID 493203 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([OH:10])=[C:4]([CH:11]([OH:15])[CH:12]([CH3:14])[CH3:13])[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>C(#N)C>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][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:15])[CH:12]([CH3:13])[CH3:14])[CH3:28]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 68725341HCID 68725341, compound

Product 1

HCID 68727506HCID 68727506, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the above prepared 4-chloro-2-(1-hydroxy-2-methyl-propyl)-5-methoxy-phenol (1.080 g, 4.68 mmol) in 15 mL acetonitrile were successively added Cs2CO3 (1.98 g, 1.3 eq.) and ethyl bromoacetate (0.596 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 1.57 g of the title compound as light brown oil, 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 1.57 g of the title compound as light brown oil

Sources & evidence

ORD record
ord-3d190cd43c714ce8b0f413c3dc7e91f9
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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