Ethyl bromoacetate → Ethyl 2-(2-formyl-4-methoxyphenoxy)acetate

HRID 493166

Reaction equation

HRID 493166 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(#N)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][O:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5])[CH3:24]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 956952-Hydroxy-5-methoxybenzaldehyde

Product 1

HCID 288667Ethyl 2-(2-formyl-4-methoxyphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-hydroxy-5-methoxybenzaldehyde (21.75 g, 143 mmol) in 240 mL acetonitrile were successively added Cs2CO3 (55.9 g, 1.2 eq.) and ethyl bromoacetate (16.6 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 and brine, drying over magnesium sulfate, and evaporation of the solvents left 34.36 g of the title product, sufficiently pure to be used for the next step.

Workup

  1. additionPouring
  2. extractionice/NH4Cl, twofold extraction with AcOEt
  3. washwashing with water and brine
  4. dry with materialdrying over magnesium sulfate, and evaporation of the solvents
  5. waitleft 34.36 g of the title product

Sources & evidence

ORD record
ord-1ccf41a1ab9f41a9ab44cb50dbf00c21
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Linked notes

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