Water → HCID 85876215, compound

HRID 1514994Notes

Reaction equation

HRID 1514994 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5].[CH3:12][O:13][C:14](=[O:17])[CH2:15]Br.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[CH3:12][O:13][C:14](=[O:17])[CH2:15][O:10][C:8]1[CH:9]=[C:2]([Cl:1])[C:3]([CH:4]=[O:5])=[C:6]([Cl:11])[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 5283822,6-Dichloro-4-hydroxybenzaldehyde

Product 1

HCID 85876215HCID 85876215, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,6-dichloro-4-hydroxybenzaldehyde (1.9 g, 10 mmol) and bromoacetic acid methyl ester (1.1 ml, 11 mmol) in DMF (20 ml) was added K2CO3 (2.8 g, 20 mmol). The suspension was stirred at ambient temperature overnight then the reaction mixture was partioned between water and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers were dried with MgSO4, filtered and concentrated. Purification by flash chromatography using heptane/EtOAc (8:1) as eluent gave (3,5-dichloro-4-formylphenoxy)-acetic acid methyl ester as a white solid.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. dry with materialthe combined organic layers were dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromatography

Sources & evidence

ORD record
ord-8c356067e51f4576b326f25fded101a1
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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