Dimethylformamide → Methyl 4-bromo-2-(difluoromethoxy)benzoate

HRID 915918Notes

Reaction equation

CN(C)C=O.[Br:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([OH:17])[CH:8]=1.Cl[C:19]([F:25])([F:24])C(OC)=O.C(=O)([O-])[O-].[K+].[K+]>O>[Br:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([O:17][CH:19]([F:25])[F:24])[CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a 70 ml dimethylformamide solution of 5.0 g (21.7 mmol) of methyl 4-bromo-2-hydroxybenzoate, 3.4 ml (32.6 mmol) of methyl chlorodifluoroacetate and 3.0 g (21.7 mmol) of potassium carbonate were added. The mixture was stirred at 60° C. for 6 hours and at room temperature for 60 hours. Then, water was added to the reaction mixture, and the mixture was extracted with ether. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. The washed system was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=8/1) to obtain 1.4 g (23%) of the captioned compound.

Workup

extractionthe mixture was extracted with ether
washThe organic layer was washed with water
dry with materialThe washed system was dried over anhydrous sodium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=8/1)

Sources & evidence

ORD record: ord-e8a9a9e944ad4f3183cb5fe249758d1d
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268128B2

Reaction notes

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