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Potassium Hydroxide → 3-(3,5-dichlorophenoxy)-4-(trifluoromethyl)pyridin-2(1H)-one

HRID 1952372
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1952372
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=2)=[C:6]([C:17]([F:20])([F:19])[F:18])[CH:5]=[CH:4][N:3]=1.[OH-:21].[K+]>C(O)(C)(C)C>[Cl:16][C:11]1[CH:10]=[C:9]([CH:14]=[C:13]([Cl:15])[CH:12]=1)[O:8][C:7]1[C:2](=[O:21])[NH:3][CH:4]=[CH:5][C:6]=1[C:17]([F:20])([F:19])[F:18]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 866463302-Chloro-3-(3,5-dichlorophenoxy)-4-(trifluoromethyl)pyridine

Produkt 1

HCID 595297703-(3,5-dichlorophenoxy)-4-(trifluoromethyl)pyridin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To 2-chloro-3-(3,5-dichlorophenoxy)-4-(trifluoromethyl)pyridine (2.10 g, 6.10 mmol) in tert-butanol (25 mL) was added potassium hydroxide (1.03 g, 18.4 mmol). The reaction mixture was placed in an oil bath and heated at 75° C. After 48 hours, the reaction mixture was allowed to cool to room temperature and was quenched with saturated aqueous ammonium chloride (25 mL) and diluted with water (25 mL). The mixture was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with water (2×50 mL) and the solvent was evaporated under reduced pressure to yield a solid. This was adsorbed onto silica and purified by column chromatography on a pre-packed silica gel Redi Sep 40 gram column, eluting with 0-5% methanol in CH2Cl2 to afford the title compound. 1H NMR (DMSO-d6) δ 12.69 (s, 1H), 7.58 (d, J=6.8 Hz, 1H), 7.32-7.30 (m, 1H), 7.10-7.08 (m, 2H), 6.48 (d, J=6.8 Hz, 1H). HRMS (M+1)=323.9800.

Aufarbeitung

  1. customThe reaction mixture was placed in an oil bath
  2. temperatureto cool to room temperature
  3. customwas quenched with saturated aqueous ammonium chloride (25 mL)
  4. additiondiluted with water (25 mL)
  5. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
  6. washThe combined organic extracts were washed with water (2×50 mL)
  7. customthe solvent was evaporated under reduced pressure
  8. customto yield a solid
  9. custompurified by column chromatography on a pre-packed silica gel Redi Sep 40 gram column
  10. washeluting with 0-5% methanol in CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-26d671dc25234f96887b148b63054e9d
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08404856B2

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