4-Fluorophenol → 4-(4-Fluorophenoxy)benzaldehyde

HRID 1394147Notes

Reaction equation

HRID 1394147 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].F[C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1>CN(C=O)C.CCOCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:16]2[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 38568024-(4-Fluorophenoxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-fluorophenol (1.06 g) in anhydrous DMF (10 mL) were added anhydrous potassium carbonate (2.07 g) and 4-fluorobenzaldehyde (1.2 g) at room temperature. The reaction was stirred at 100° C. for 16 h, then cooled to room temperature and diluted with ether. The organic layer was washed with 1N sodium hydroxide, and then with water, dried over sodium sulphate, and concentrated under reduced pressure. The crude aldehyde obtained was purified by flash-column chromatography on silica-gel using 20% EtOAc in hexanes to provide the pure aldehyde.

Workup

  1. temperaturecooled to room temperature
  2. washThe organic layer was washed with 1N sodium hydroxide
  3. dry with materialwith water, dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude aldehyde obtained
  6. customwas purified by flash-column chromatography on silica-gel

Sources & evidence

ORD record
ord-4b777751155f492480087b5dd69aa19e
Source dataset
uspto-grants-2008_03
Patent number
US07348348B2

Reaction notes

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