Potassium Carbonate → HCID 68463174, compound

HRID 499726Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][C:5]=1[Br:11].[CH2:13]([C:15]1[CH:20]=[CH:19][C:18](O)=[CH:17][CH:16]=1)[CH3:14].C(=O)([O-])[O-:23].[K+].[K+].[Cl-].[NH4+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:23][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH2:13][CH3:14])=[CH:6][C:5]=1[Br:11]

Participants

Conditions

Temperature: 160 °C

Procedure

To a solution of 2-bromo-4-fluoro-benzoic acid methyl ester (488 mg, 2.09 mmol) in anhydrous DMF (15 ml), 4-ethylphenol (256 mg, 2.09 mmol) and potassium carbonate (289 mg, 2.09 mmol) were added at room temperature, followed by stirring under a nitrogen atmosphere for 16 hours at 160° C. The reaction mixture was cooled and, after addition of saturated aqueous ammonium chloride, was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:20)) to give the titled compound (455 mg, 65%).

Workup

temperatureThe reaction mixture was cooled
extractionwas then extracted with ethyl acetate
washThe organic layer was washed with saturated aqueous sodium chloride
dry with materialdried over sodium sulfate
filtrationAfter filtration
distillationthe solvent was distilled off under reduced pressure
customthe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:20))

Sources & evidence

ORD record: ord-01d65c7f8d074b0b874a3b0de24da1ed
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767651B2

Reaction notes

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