4-Methoxyphenol → 3-Fluoro-4-(4-methoxy-phenoxy)-benzaldehyde

HRID 1406335Notes

Reaction equation

HRID 1406335 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[F:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1F)[CH:14]=[O:15]>CC(N(C)C)=O>[F:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[O:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH:14]=[O:15]

Participants

4

Reactant 2

HCID 90154-MethoxyphenolHCID 5880883,4-Difluorobenzaldehyde

Product 1

HCID 286041023-Fluoro-4-(4-methoxy-phenoxy)-benzaldehyde

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

4.9 g (40 mmol) of 4-methoxy-phenol and 4.4 ml (40 mmol) of 3,4-difluorobenzaldehyde were dissolved in 40 ml DMA and stirred in a microwave (CEM Explorer) for 15 minutes at 110° C., then filtered through basic Alox, washed with DMF and concentrated by rotary evaporation. The residue was separated through a KG column with a gradient (cyclohexane+10-25% ethyl acetate) and concentrated by rotary evaporation.

Workup

  1. filtrationfiltered through basic Alox
  2. washwashed with DMF
  3. concentrationconcentrated by rotary evaporation
  4. customThe residue was separated through a KG column with a gradient (cyclohexane+10-25% ethyl acetate)
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-6d694ab1a44541eebdc880fadf9c7f6a
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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