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Water → Methyl {o-{5-[(2-chloro-alpha,alpha,alpha-trifluoro-p-tolyl)oxy]-2-nitrophenoxy}phenoxy}acetate

HRID 21517
Notes
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Reaction equation

HRID 21517 reaction equation
F[C:2]1[CH:3]=[C:4]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[C:14]([Cl:22])[CH:13]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[OH:23][C:24]1[CH:35]=[CH:34][CH:33]=[CH:32][C:25]=1[O:26][CH2:27][C:28]([O:30][CH3:31])=[O:29].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[Cl:22][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)[O:23][C:24]2[CH:35]=[CH:34][CH:33]=[CH:32][C:25]=2[O:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH:17]=[CH:16][C:15]=1[C:18]([F:21])([F:20])[F:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 23202292-(Methoxycarbonyl)methoxyphenolHCID 867487152-Chloro-alpha,alpha,alpha-trifluoro-p-tolyl 3-fluoro-4-nitrophenyl ether

Product 1

HCID 86748714Methyl {o-{5-[(2-chloro-alpha,alpha,alpha-trifluoro-p-tolyl)oxy]-2-nitrophenoxy}phenoxy}acetateYield 20.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-chloro-α,α,α-trifluoro-p-tolyl 3-fluoro-4-nitrophenyl ether (1.0 g, 3.0 mmol), methyl (o-hydroxyphenoxy)acetate (0.81 g, 4.5 mmol) and potassium carbonate (0.62 g, 4.5 mmol) in N,N-dimethylformamide is heated at 50° C. for 18 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 white oil. Column chromatography of the oil using silica gel and a 15% ethyl acetate in hexanes solution gives the title product as a clear liquid (0.3 g) which is identified by 1HNMR and 13CNMR spectral analyses.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ether
  3. extractionThe organic extract
  4. washis washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a white oil

Sources & evidence

ORD record
ord-a8934729cf91430db8240c4c4def6326
Source dataset
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05424280

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes