Potassium Carbonate → 5-bromo-2-(5-methyl-1H-imidazol-1-yl)benzonitrile

HRID 1446453Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11](F)=[C:12]([CH:15]=1)[C:13]#[N:14].[CH3:17][C:18]1[N:19]=[CH:20][NH:21][CH:22]=1>CN(C=O)C>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([N:19]2[C:18]([CH3:17])=[CH:22][N:21]=[CH:20]2)=[C:12]([CH:15]=1)[C:13]#[N:14]

Participants

Conditions

Temperature: 100 °C

Procedure

Potassium carbonate (2.07 g) was added to a DMF (20 mL) solution of 5-bromo-2-fluorobenzonitrile (2.00 g) and 4-methylimidazole (1.23 g) and the reaction solution was agitated at 100° C. for 4.5 hours. The reaction mixture was concentrated under reduced pressure, water and ethyl acetate were added to the residue, and the organic layer was partitioned. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent:hexane-ethyl acetate system), and 5-bromo-2-(4-methyl-1H-imidazol-1-yl)benzonitrile (962 mg) and 5-bromo-2-(5-methyl-1H-imidazol-1-yl)benzonitrile (60 mg) were obtained.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure, water and ethyl acetate
additionwere added to the residue
customthe organic layer was partitioned
washThe organic layer was washed with a saturated saline solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (elution solvent:hexane-ethyl acetate system), and 5-bromo-2-(4-methyl-1H-imidazol-1-yl)benzonitrile (962 mg)

Sources & evidence

ORD record: ord-1eaa7cf9da5d426b9ace2b3b0fca8896
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07667041B2

Reaction notes

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