Calcium Fluoride → Methyl 4-(fluoromethyl)benzoate

HRID 1794248

Reaktionsgleichung

Reaktionsgleichung von HRID 1794248
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[F-:13].[K+].[F-].[Ca+2].[F-]>C(#N)C>[F:13][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 84512Calcium FluorideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 522689Potassium Fluoride

Produkt 1

HCID 21866613Methyl 4-(fluoromethyl)benzoateAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Dry acetonitrile (150 ml) was added to 25.00 g of methyl 4-(bromomethyl)benzoate, 19.02 g of potassium fluoride and 9.51 g of calcium fluoride, and the mixture was heated to reflux for 3 days. The reaction solution was concentrated. After addition of 200 ml of acetonitrile, insolubles were removed by filtration, and the filtrate was concentrated again. The residue was purified by silica gel column chromatography (YMC.GEL® SIL-60-230/70, n-hexane:ethyl acetate=10:1–4:1), followed by distillation under reduced pressure to provide 14.45 g of the objective compound as colorless oil. B.p. 118.5–119° C./18 mmHg.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 days
  3. concentrationThe reaction solution was concentrated
  4. additionAfter addition of 200 ml of acetonitrile, insolubles
  5. customwere removed by filtration
  6. concentrationthe filtrate was concentrated again
  7. customThe residue was purified by silica gel column chromatography (YMC.GEL® SIL-60-230/70, n-hexane:ethyl acetate=10:1–4:1)
  8. distillationfollowed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a56bed9b33354949889367df0cd190f3
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07022723B2

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