Water → Methyl {o-{5-{[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxy}-2-nitrophenoxy}phenoxy}acetate

HRID 21518Notes

Reaction equation

F[C:2]1[CH:3]=[CH:4][C:5]([N+:21]([O-:23])=[O:22])=[C:6]([CH:20]=1)[O:7][C:8]1[CH:19]=[CH:18][CH:17]=[CH:16][C:9]=1[O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13].[CH3:24][N:25]1[C:29]([C:30]([F:33])([F:32])[F:31])=[CH:28][C:27]([OH:34])=[N:26]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[CH3:24][N:25]1[C:29]([C:30]([F:31])([F:32])[F:33])=[CH:28][C:27]([O:34][C:2]2[CH:3]=[CH:4][C:5]([N+:21]([O-:23])=[O:22])=[C:6]([CH:20]=2)[O:7][C:8]2[CH:19]=[CH:18][CH:17]=[CH:16][C:9]=2[O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[N:26]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of methyl [o-(5-fluoro-2-nitrophenoxy)phenoxy]acetate (1.1 g, 3.4 mmol), 1-methyl-5-(trifluoromethyl)pyrazol-3-ol (0.63 g, 3.8 mmol) and potassium carbonate (0.53 g, 3.8 mmol) in N,N-dimethylformamide is stirred at 100° C. for 18 hours, cooled to room temperature, poured into water and extracted with ethyl acetate. The organic extract is washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain an orange oil. Column chromatography of the oil using silica gel and a 30% ethyl acetate in hexanes solution gives the title product as a yellow oil (0.5 g) which is identified by 1HNMR and 13CNMR spectral analyses.

Workup

temperaturecooled to room temperature
extractionextracted with ethyl acetate
extractionThe organic extract
washis washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customto obtain an orange oil

Sources & evidence

ORD record: ord-46647fc881914ca98a879d80d107cc7d
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05424280

Reaction notes

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