Water → Methyl {o-{5-{[3-chloro-5-(trifluoromethyl)-2-pyridyl]oxy}-2-nitrophenoxy}phenoxy}acetate

HRID 21516

Reaction equation

[OH:1][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].Cl[C:25]1[C:30]([Cl:31])=[CH:29][C:28]([C:32]([F:35])([F:34])[F:33])=[CH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:31][C:30]1[C:25]([O:1][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][CH:27]=[C:28]([C:32]([F:34])([F:33])[F:35])[CH:29]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of methyl [o-(5-hydroxy-2-nitrophenoxy)phenoxy]acetate (1.9 g, 5.9 mmol), 2,3-di-chloro-5-(trifluoromethyl)pyridine (1.92 g, 8.9 mmol) and potassium carbonate (1.23 g, 8.9 mmol) in N,N-di-methylformamide is heated at 100° C. for 12 hours, cooled to room temperature, poured into water and extracted with ether. The organic extract is washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a yellow oil. Flash chromatography of the oil using silica gel and a (1:4) ethyl acetate/hexanes solution gives the title product as a yellow liquid (0.8 g) which is identified by 1HNMR and 13CNMR spectral analyses.

Workup

temperaturecooled to room temperature
extractionextracted with ether
extractionThe organic extract
washis washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customto obtain a yellow oil

Sources & evidence

ORD record: ord-0ea58b021f504387a450c1fee6fddaa9
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05424280

Linked notes

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