Water → 2-Chloro-5-fluoro-4-hydroxybenzaldehyde

HRID 253441Notes

Reaction equation

HRID 253441 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].C[O:13]CCOCCO.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[C:8]([OH:13])[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 597748312-Chloro-5-fluoro-4-hydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To 2-chloro-4,5-difluoro-benzaldehyde (110, 0.40 g, 2.30 mmol, prepared as described in Example 37) in N,N-dimethylformamide (10.0 mL) were added 2-(2-methoxyethoxy)-ethanol, (0.327 g, 2.72 mmol) and cesium carbonate (0.886 g, 2.72 mmol). 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 anhydrous 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 (111, 0.24 g, 61.0%). MS (ESI) [M+H+]+=173.1.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous 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 (111, 0.24 g, 61.0%)

Sources & evidence

ORD record
ord-013b2d1d8f044bdf982b6428723deb1d
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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