Dimethylformamide → 4-(4-Fluorophenoxy)benzaldehyde

HRID 640418Notes

Reaction equation

HRID 640418 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-350c1a1da97b436cbc46bb8f1ebc0b2d
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

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