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Potassium Fluoride → ((S)-2-Fluoro-1-methyl-ethyl)-benzene

HRID 870335
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 870335
[C:1]1([C@H:7]([CH3:20])[CH2:8]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-:21].[K+]>[Cl-].[Na+]>[F:21][CH2:8][C@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 522689Potassium FluorideHCID 13791931Toluene-4-sulfonic acid (S)-2-phenyl-propyl ester

Produkt 1

HCID 53628601((S)-2-Fluoro-1-methyl-ethyl)-benzeneAusbeute 62,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5234Sodium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
62.5 °C

Versuchsvorschrift

9.62 g of toluene-4-sulfonic acid (S)-2-phenyl-propyl ester (33.13 mmol) were dissolved in 80 ml of polyethyleneglycol 400. 9.62 g of potassium fluoride (165.6 mmol) were added and the reaction mixture was stirred at 50° C. for 3 days and another 2 days at 55-70° C. The reaction was treated with 150 ml of saturated aqueous sodium chloride solution, extracted three times with diethyl ether, and the combined organic layers were dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The crude product was purified via silica gel chromatography using cyclohexane/ethyl acetate 15% as eluent. 2.85 g of the desired product were isolated, containing ˜25% of the elimination side product.

Aufarbeitung

  1. extractionextracted three times with diethyl ether
  2. dry with materialthe combined organic layers were dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure
  5. customThe crude product was purified via silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-aca7b4f44b014699b7dab0bcaa9a01df
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08969552B2

Notizen zur Reaktion

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