4-Iodophenol → 2-(4-Iodophenoxy)benzaldehyde

HRID 51483Notes

Reaction equation

HRID 51483 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.F[C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=[O:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 14909242-(4-Iodophenoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-iodophenol (25.0 g), 2-fluorobenzaldehyde (14.14 g), potassium carbonate (31.5 g) and dimethylformamide (500 ml) was heated at 120° C. under nitrogen with stirring for 15 hours. The mixture was cooled to ambient temperature and filtered. Water (500 ml) was added to the filtrate and the mixture was extracted with ethyl acetate to give a solid which was triturated with hot hexane (500 ml). The supernatant liquid was decanted from a residual gum and cooled. The solid which precipitated was collected by filtration to give 2-(4-iodophenoxy) benzaldehyde, m.p. 84.5-86° C.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. additionWater (500 ml) was added to the filtrate
  4. extractionthe mixture was extracted with ethyl acetate
  5. customto give a solid which
  6. customwas triturated with hot hexane (500 ml)
  7. customThe supernatant liquid was decanted from a residual gum
  8. temperaturecooled
  9. customThe solid which precipitated
  10. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-7fe1ab5cd2914eb199377ade391620fb
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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