Trifluoroacetic anhydride → 2-Chloro-5-(trifluoromethyl)pyridine 1-oxide

HRID 659982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 659982
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.NC(N)=[O:14].OO.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][N+:3]=1[O-:14]

Komponenten

5

Edukt 3

HCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 923422-Chloro-5-(trifluoromethyl)pyridine

Produkt 1

HCID 154483422-Chloro-5-(trifluoromethyl)pyridine 1-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-Chloro-5-trifluoromethyl-pyridine (16, 10 mmol) was dissolved in CH2Cl2 (20 mL) and UHP (Urea-hydrogen peroxide addition compound, 21 mmol) was added. The mixture was cooled to 0° C., trifluoroacetic anhydride (20 mmol) was then slowly added to the reaction mixture. It was allowed to warm to room temperature and stirred until the reaction was completed judged by TLC. The reaction was quenched with aqueous Na2SO3, stirred for 4 h, washed with saturated aqueous NaHCO3, and dried over anhydrous MgSO4. Column chromatography afforded 1.8 g of compound 17 as oil.

Aufarbeitung

  1. additionwas added
  2. temperatureto warm to room temperature
  3. customThe reaction was quenched with aqueous Na2SO3
  4. stirringstirred for 4 h
  5. washwashed with saturated aqueous NaHCO3
  6. dry with materialdried over anhydrous MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-a3f42d8db40c4f96964299b8edb84aba
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084454B2

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