Water → 2-Chloro-5-fluoro-4-[2-(2-methoxy-ethoxy)-ethoxy]-benzaldehyde

HRID 253440Notes

Reaction equation

HRID 253440 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8](F)[C:7]([F:11])=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][OH:19].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[C:8]([O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH3:12])[C:7]([F:11])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8134Diethylene Glycol Monomethyl EtherHCID 10796Cesium carbonateHCID 152947152-Chloro-4,5-difluorobenzaldehyde

Product 1

HCID 598038062-Chloro-5-fluoro-4-[2-(2-methoxy-ethoxy)-ethoxy]-benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To 2-chloro-4,5-difluoro-benzaldehyde (110, 0.40 g, 0.0023 mol) in N,N-dimethylformamide (10.0 mL), 2-(2-methoxyethoxy)-ethanol (0.327 g, 2.72 mmol) and cesium carbonate (0.886 g, 2.72 mmol) were added. The reaction was stirred at 90° C. overnight. The reaction was poured into water, acidified to pH around 5, and extracted with ethyl acetate. The organic layer was dried over an hydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give a white solid (121, 0.15 g, 24.0%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over an hydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 30% ethyl acetate in hexane
  7. customto give a white solid (121, 0.15 g, 24.0%)

Sources & evidence

ORD record
ord-adc3637e0fb5482fa612873b94f9453a
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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