Dimethylformamide → 4-(4-Fluorophenoxy)benzaldehyde

HRID 78135Notes

Reaction equation

HRID 78135 reaction equation
CN(C)C=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.F[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>O>[F:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 38568024-(4-Fluorophenoxy)benzaldehydeYield 94.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To an N,N-dimethylformamide (40.0 mL) solution of 4-fluorophenol (5.00 g, 44.6 mmol) and 4-fluorobenzaldehyde (4.00 mg, 32.2 mmol) was added potassium carbonate (13.4 g, 96.6 mmol), which was stirred for 21 hours at 80° C. The reaction solution was then cooled to room temperature, water was added thereto, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate: heptane=1:15→1:10) to obtain the title compound (6.60 g, 90.1%).

Workup

  1. temperatureThe reaction solution was then cooled to room temperature
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. customthe solvent was evaporated under a reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate: heptane=1:15→1:10)

Sources & evidence

ORD record
ord-35932da93644434db88647a26c3d1609
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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