Imidazole → 3-Chloro-4-(1H-imidazol-1-YL)benzaldehyde

HRID 2247466Notes

Reaction equation

CN(C=O)C.[Cl:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1F)[CH:10]=[O:11].C(=O)([O-])[O-].[K+].[K+].[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1>C(OCC)(=O)C.O>[Cl:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)[CH:10]=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

To a DMF (20 mL) solution of 3-chloro-4-fluorobenzaldehyde (500 mg), potassium carbonate (1.20 g) and imidazole (275 mg) were added one by one, and the reaction solution was agitated at 80° 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 obtained residue was purified by silica gel chromatography (elution solvent: ethyl acetate->ethyl acetate:methanol=10:1), and 548 mg 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 obtained residue was purified by silica gel chromatography (elution solvent: ethyl acetate->ethyl acetate:methanol=10:1)

Sources & evidence

ORD record: ord-f6a3889bda7a470daf015185ace7acca
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687640B2

Reaction notes

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