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Water → Methyl [2-(5-acetylamino-4-fluoro-2-nitrophenoxy)phenoxy]acetate

HRID 493937
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 493937
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[OH:18])=[CH:4][C:3]=1[NH:19][C:20](=[O:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]([O:33][CH3:34])=[O:32].O>CN(C)C=O>[C:20]([NH:19][C:3]1[C:2]([F:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[C:5]([CH:4]=1)[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:30][C:31]([O:33][CH3:34])=[O:32])(=[O:22])[CH3:21]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 21933568N-[2-fluoro-5-(2-hydroxyphenoxy)-4-nitrophenyl]acetamide

Produkt 1

HCID 21053883Methyl [2-(5-acetylamino-4-fluoro-2-nitrophenoxy)phenoxy]acetateAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

First, 3.02 g of N-[2-fluoro-5-(2-hydroxyphenoxy)-4-nitrophenyl]acetamide was dissolved in 20 ml of N,N-dimethylformamide, to which 1.5 g of potassium carbonate was added, and the mixture was stirred at room temperature for 1 hour. Then, 1.6 g of methyl bromoacetate was added at room temperature. After stirring at the same temperature for 2 hours, the mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with diluted hydrochloric acid and water, dried over magnesium sulfate, and then concentrated. The resulting crystals were washed with t-butyl methyl ether to give 3.01 g of methyl [2-(5-acetylamino-4-fluoro-2-nitrophenoxy)phenoxy]acetate.

Aufarbeitung

  1. additionwas added
  2. stirringAfter stirring at the same temperature for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with diluted hydrochloric acid and water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. washThe resulting crystals were washed with t-butyl methyl ether

Quellen und Nachweise

ORD-Eintrag
ord-41d3880ab24243b2b46ca1fe62ef1891
Quelldatensatz
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07538072B2

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