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Pyridine → 4-tert-Butyl-2-nitrophenyl trifluoromethanesulfonate

HRID 735790
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 735790
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[C:16]([C:20]1[CH:25]=[CH:24][C:23](O)=[C:22]([N+:27]([O-:29])=[O:28])[CH:21]=1)([CH3:19])([CH3:18])[CH3:17].N1C=CC=CC=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:16]([C:20]1[CH:25]=[CH:24][C:23]([O:8][S:1]([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2])=[C:22]([N+:27]([O-:29])=[O:28])[CH:21]=1)([CH3:19])([CH3:17])[CH3:18]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 18661Phenol, 4-(1,1-dimethylethyl)-2-nitro-HCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 231090154-tert-Butyl-2-nitrophenyl trifluoromethanesulfonateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Triflic anhydride (4.14 mL, 24.6 mmol) was added dropwise to a solution of 4-tert-butyl-2-nitrophenol (4.00 g, 20.5 mmol) and pyridine (2.16 mL, 26.7 mmol) in methylene chloride (50 mL) at 0° C. The yellow solution was stirred 0.25 h at 0° C., poured onto saturated aqueous NaHCO3 and extracted with methylene chloride. The combined extracts were washed with saturated aqueous NaHCO3, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by filtration through a plug of silica-gel (methylene chloride) to provide trifluoro-methanesulfonic acid 4-tert-butyl-2-nitro-phenyl ester (5.82 g, 87%) as a pale yellow oil which was utilized without further purification.

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. washThe combined extracts were washed with saturated aqueous NaHCO3
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationThe residue was purified by filtration through a plug of silica-gel (methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-92b71e5b944a48ada13a8cc0ebbbeb58
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07592332B2

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