Water → 3-(4-nitrophenoxy)-N-[4-(trifluoromethyl)phenyl]benzamide

HRID 2190419Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1)=[O:6].C(=O)([O-])[O-].[K+].[K+].F[C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=1.O>CN(C)C=O>[N+:34]([C:31]1[CH:32]=[CH:33][C:28]([O:1][C:2]2[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=2)[C:5]([NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:12][CH:13]=2)=[O:6])=[CH:29][CH:30]=1)([O-:36])=[O:35]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 3-hydroxy-N-[4-(trifluoromethyl)phenyl]benzamide (5.62 g, 20.0 mmol) and potassium carbonate (2.76 g, 20.0 mmol) in N,N-dimethylformamide (20 mL) was added 1-fluoro-4-nitrobenzene (3.10 g, 22.0 mmol), and the mixture was stirred at 60° C. for 18 hr. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane/ethyl acetate=1:1), and triturated with diethyl ether to give the title compound (6.75 g, 84%) as a white solid.

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent:hexane/ethyl acetate=1:1)
customtriturated with diethyl ether

Sources & evidence

ORD record: ord-544a5b67df6545e4ac21f63615dd3531
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324395B2

Reaction notes

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