Ethyl Acetate → Methyl {p-{5-[(2-chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl)oxy]-2-nitroanilino}phenoxy}acetate

HRID 21519Notes

Reaction equation

F[C:2]1[CH:3]=[C:4]([O:11][C:12]2[CH:17]=[C:16]([F:18])[C:15]([C:19]([F:22])([F:21])[F:20])=[C:14]([Cl:23])[CH:13]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[NH2:24][C:25]1[CH:36]=[CH:35][C:28]([O:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.[Cl-].[Na+].O>[Cl:23][C:14]1[CH:13]=[C:12]([O:11][C:4]2[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH:3]=2)[NH:24][C:25]2[CH:26]=[CH:27][C:28]([O:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:35][CH:36]=2)[CH:17]=[C:16]([F:18])[C:15]=1[C:19]([F:20])([F:22])[F:21]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-chloro-α,α,α,6-tetrafluoro-p-tolyl 3-fluoro-4-nitrophenyl ether (2.1 g, 0.006 mol), methyl (p-aminophenoxy)acetate (2.7 g, 0.015 mol) and potassium carbonate (2.0 g, 0,015 mol) in N,N-dimethyl formamide is stirred at 80° C. for 18 hours, cooled to room temperature, poured into brine and extracted with ethyl acetate. The organic extract is washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. Flash chromatography of the residue using silica gel and a 20% ethyl acetate in hexanes solution gives the title product as a red oil (0.6 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 a residue

Sources & evidence

ORD record: ord-83e80843e5f64dcf9c75d52225a97513
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05424280

Reaction notes

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