Imidazole → Benzaldehyde, 3-fluoro-4-(1H-imidazol-1-yl)-

HRID 2247490Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.CN(C=O)C.[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1F)[CH:21]=[O:22]>C(OCC)(=O)C.O>[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1)[CH:21]=[O:22]

Participants

Conditions

Temperature: 100 °C

Procedure

Potassium carbonate (1.71 g) and imidazole (847 mg) were added to a DMF (20 mL) solution of 3,4-difluorobenzaldehyde (2.0 g). The reaction solution was agitated at 100° C. overnight, water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: hexane:ethyl acetate=1:1->ethyl acetate), and 1.11 g of the title compound was obtained. The physical properties of the compound are as follows.

Workup

customthe organic layer was partitioned
washAfter the obtained organic layer was washed with a saturated saline solution, it
dry with materialwas dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (elution solvent: hexane:ethyl acetate=1:1->ethyl acetate)

Sources & evidence

ORD record: ord-95c0c783859d405db9daa49aca1910c4
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687640B2

Reaction notes

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