Carbon Dioxide → 2-Fluoro-5-(trifluoromethoxy)benzaldehyde

HRID 1786218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1786218
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.C([Li])(C)(C)C.[C:18](=O)=[O:19].CN(C=O)C>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]([F:10])([F:11])[F:12])=[CH:6][C:7]=1[CH:18]=[O:19]

Komponenten

6

Edukt 4

HCID 280Carbon DioxideHCID 6228DimethylformamideHCID 676984-(Trifluoromethoxy)fluorobenzeneHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 27833242-Fluoro-5-(trifluoromethoxy)benzaldehydeAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1-fluoro-4-trifluoromethoxy-benzene (21.0 g, 117 mmol) in THF (233 mL) was cooled to <−70° C. and tert.-butyllithium (86 mL, 1.5 M in pentane, 129 mmol) was added at such a rate that temperature was kept <−70° C. Stirring in the dry ice bath was continued for 15 min, then DMF (11.6 mL, 150 mmol) was added dropwise keeping temperature <−70° C. After 30 min the reaction mixture was allowed to reach rt, quenched with saturated NH4Cl solution and extracted with diethylether. The organic phase was washed with brine, concentrated and chromatographed (SiO2, heptanes:ethyl acetate=100:0 to 80:2) to afford the title compound (11.0 g, 53%) as a light yellow oil. 1H-NMR (300 MHz, DMSO): δ=7.60 (t, J=9.2 Hz, 1H), 7.75-7.85 (m, 2H), 10.20 (s, 1H).

Aufarbeitung

  1. customwas kept <−70° C
  2. customtemperature <−70° C
  3. waitAfter 30 min the reaction mixture was allowed
  4. customto reach rt
  5. customquenched with saturated NH4Cl solution
  6. extractionextracted with diethylether
  7. washThe organic phase was washed with brine
  8. concentrationconcentrated
  9. customchromatographed (SiO2, heptanes:ethyl acetate=100:0 to 80:2)

Quellen und Nachweise

ORD-Eintrag
ord-953fd019dabd4558a10ba291c9bfb23d
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07507729B2

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