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Pyridine → Methyl 5-{[(trifluoromethyl)sulfonyl]oxy}biphenyl-3-carboxylate

HRID 1096950
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1096950
N1C=CC=CC=1.[F:7][C:8]([F:21])([F:20])[S:9]([O:12]S(C(F)(F)F)(=O)=O)(=[O:11])=[O:10].O[C:23]1[CH:24]=[C:25]([C:35]([O:37][CH3:38])=[O:36])[CH:26]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:28]=1.[Cl-].[NH4+]>C(Cl)(Cl)Cl>[F:7][C:8]([F:21])([F:20])[S:9]([O:12][C:23]1[CH:24]=[C:25]([C:35]([O:37][CH3:38])=[O:36])[CH:26]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:28]=1)(=[O:11])=[O:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 25517Ammonium ChlorideHCID 67749Trifluoromethanesulfonic anhydrideHCID 18945322Methyl 3-hydroxy-5-phenylbenzoate

Produkt 1

HCID 57930914Methyl 5-{[(trifluoromethyl)sulfonyl]oxy}biphenyl-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212
Chloroform
Lösungsmittel

Versuchsvorschrift

With cooling with ice, pyridine (1.2 mL) and trifluoromethanesulfonic acid anhydride (1.2 mL) were added to a CHCl3 (40 mL) solution of methyl 5-hydroxybiphenyl-3-carboxylate, and stirred for 30 minutes with cooling with ice. Aqueous ammonium chloride was added to the reaction liquid, extracted with ethyl acetate, and the organic layer was washed with water, aqueous saturated sodium bicarbonate solution and saturated saline water. This was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the title compound as a yellow oil. Not purified, this was used in the next step.

Aufarbeitung

  1. temperaturewith cooling with ice
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with water, aqueous saturated sodium bicarbonate solution and saturated saline water
  4. dry with materialThis was dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c681af8e231949be8797ae88eb495444
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08138197B2

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