Dimethylformamide → (4-Trifluoromethoxyphenoxy)-acetic acid tert-butyl ester

HRID 1009191Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009191
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].C(=O)([O-])[O-].[K+].[K+].[F:16][C:17]([F:27])([F:26])[O:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1.CN(C=O)C>CCOC(C)=O.O>[C:6]([O:5][C:3](=[O:4])[CH2:2][O:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][C:17]([F:16])([F:26])[F:27])=[CH:20][CH:21]=1)([CH3:9])([CH3:8])[CH3:7]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 70015p-(Trifluoromethoxy)phenolHCID 79177tert-Butyl bromoacetate

Produkt 1

HCID 57787045(4-Trifluoromethoxyphenoxy)-acetic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

tert-Butyl bromoacetate was added to a stirring suspension of potassium carbonate (14.6 g, 106 mmol), 4-(trifluoromethoxy)phenol (15.7 g, 88 mmol) and DMF (50 mL). The reaction mixture was stirred for 12 hours. The mixture was diluted with EtOAc and water. The layers were separated and the aqueous layer was extracted with 3×EtOAc. The combined organic layers were washed with 5% aqueous lithium chloride and brine, dried over sodium sulfate, filtered, and reduced in vacuo to afford the title compound as a colorless oil: 1H NMR (400 MHz, d6-DMSO): 7.27 (d, 2H), 6.98 (d, 2H), 4.68 (s, 2H), 1.42 (s, 9H).

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with 3×EtOAc
  3. washThe combined organic layers were washed with 5% aqueous lithium chloride and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-9f1591b153c64893a0d8b6f11fffc652
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973061B2

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