Water → 2-(3,5-dichloro-4-formylphenoxy)-N,N-dimethyl-acetamide

HRID 1515020Notes

Reaction equation

HRID 1515020 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].Cl[CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15].O.CCOC(C)=O>CN(C=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5])[O:10][CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 758862-chloro-N,N-dimethylacetamideHCID 5283822,6-Dichloro-4-hydroxybenzaldehyde

Product 1

HCID 866512742-(3,5-dichloro-4-formylphenoxy)-N,N-dimethyl-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6-dichloro-4-hydroxybenzaldehyde (250 mg, 1.31 mmol) and 2-chloro-N,N-dimethylacetamide (238 mg, 1.97 mmol) in DMF (10 mL) was added CsCO3 (854 mg, 2.62 mmol) and the suspension was stirred at ambient temperature overnight. The reaction mixture was partioned between water and EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layers were dried with MgSO4, filtered and concentrated. The material was purified by flash chromatography using heptane/EtOAc (1:3) as eluent to give 2-(3,5-dichloro-4-formylphenoxy)-N,N-dimethyl-acetamide as a yellow 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. customThe material was purified by flash chromatography

Sources & evidence

ORD record
ord-73402ef68de94c42861d01ddcc815169
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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