Water → 2-Ethenyl-3-fluorobenzaldehyde

HRID 1770406Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1770406
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]=[CH2:10].C([Li])CCC.CN(C)[CH:18]=[O:19].O>C1COCC1>[F:8][C:4]1[C:3]([CH:9]=[CH2:10])=[C:2]([CH:7]=[CH:6][CH:5]=1)[CH:18]=[O:19]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 6228DimethylformamideHCID 672377801313010-16-0HCID 178418339Butyllithium

Produkt 1

HCID 866575712-Ethenyl-3-fluorobenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 1-bromo-3-fluoro-2-vinylbenzene (900 mg) in THF (40 ml) was added dropwise, at −78° C., n-butyllithium (3.4 ml 1.6 M/hexane). After 60 minutes, N,N-dimethylformamide (0.69 ml) was added dropwise at −78° C. After stirring at −78° C. for 60 minutes, the reaction mixture was admixed with water and then warmed to room temperature. Then the mixture was admixed with water and extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated. Purification by column chromatography gives 3-fluoro-2-vinylbenzaldehyde (160 mg).

Aufarbeitung

  1. temperaturewarmed to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. concentrationconcentrated
  5. customPurification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-acfc42632cdb4413a41b3db25de31c4f
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09247748B2

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