Ethyl Acetate → 3-Fluoro-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

HRID 1436137Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[CH:5]=[O:6].[CH3:11][C:12]1[N:13]=[CH:14][NH:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:15]1[CH:16]=[C:12]([CH3:11])[N:13]=[CH:14]1)[CH:5]=[O:6]

Participants

Conditions

Temperature: 90 °C

Procedure

3,4-Difluorobenzaldehyde (30.0 g) was dissolved in DMF (400 mL), and 4-methyl-1H-imidazole (34.8 g) and potassium carbonate (58.5 g) were added to the solution at room temperature. The reaction solution was stirred at 90° C. for six hours. The reaction solution was left to cool to room temperature. Then, ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system), solidified with tert-butyl methyl ether, and separated by filtration to obtain 6.28 g of the title compound. The property values of the compound are as follows.

Workup

waitThe reaction solution was left
temperatureto cool to room temperature
customthe organic layer was separated
washThe resulting organic layer was washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)
customseparated by filtration

Sources & evidence

ORD record: ord-2139535505da4d458c996a1b3e7ddebe
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618960B2

Reaction notes

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