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

HRID 16328

Reaction equation

[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1F)[CH:22]=[O:23]>O.C(OCC)(=O)C>[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[N:5]1[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]1)[CH:22]=[O:23]

Participants

Conditions

Temperature: 90 °C

Procedure

4-Methylimidazole (46.4 g) and potassium carbonate (78.0 g) were added to a DMF solution (533 mL) of 3,4-difluorobenzaldehyde (40.0 g) at room temperature. This reaction solution was stirred at 90° C. for 6 hr and then was allowed to cool to room temperature. To the reaction solution, ethyl acetate and water were added. The organic layer was separated, washed with saturated saline, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: heptane-ethyl acetate system) and further solidified with tert-butylmethylether to give 10.1 g of the title compound. The physical property values of this compound were as follows:

Workup

temperatureto cool to room temperature
customThe organic layer was separated
washwashed with saturated saline
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluting solvent: heptane-ethyl acetate system) and further solidified with tert-butylmethylether

Sources & evidence

ORD record: ord-c7bc762f2f1545c5a7b5de280b391cda
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737141B2

Linked notes

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