Hydrochloric Acid → 2,2-Difluoro-benzo(1,3)dioxole-4-carbaldehyde

HRID 37585

Reaktionsgleichung

Reaktionsgleichung von HRID 37585
C([Li])CCC.CN(C)CCN(C)C.[F:14][C:15]1([F:24])[O:19][C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[O:16]1.CN([CH:28]=[O:29])C.Cl>C1(C)C=CC=CC=1>[CH:21]1[CH:20]=[C:18]2[O:19][C:15]([F:14])([F:24])[O:16][C:17]2=[C:23]([CH:28]=[O:29])[CH:22]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 741032,2-Difluoro-1,3-benzodioxoleHCID 178418339Butyllithium

Produkt 1

HCID 27369702,2-Difluoro-benzo(1,3)dioxole-4-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

94.0 g (272 mmol) of n-butyllithium (18.5% in toluene) are added dropwise under a nitrogen atmosphere, at from -15° to -10° C., over a period of 1.5 hours, to 29.5 g (254 mmol) of N,N,N',N'-tetramethylethylenediamine and 40.0 g (253 mmol) of 2,2-difluoro-1,3-benzodioxole in 35 ml of toluene, an orange suspension being formed. 19.7 g (270 mmol) of DMF are then metered in at from -15° to -10° C. over a period of 1/2 hour. The pale yellow suspension is poured at +10° C. onto 346 g (1.105 mol) of 11.6% aqueous hydrochloric acid and the whole is stirred for 1/2 hour to complete the reaction. The aqueous phase is separated off and the organic phase is concentrated by evaporation in a vacuum rotary evaporator at 50° C./200 mbar under nitrogen to yield the desired product.

Aufarbeitung

  1. customan orange suspension being formed
  2. customthe reaction
  3. customThe aqueous phase is separated off
  4. concentrationthe organic phase is concentrated by evaporation in a vacuum rotary evaporator at 50° C./200 mbar under nitrogen

Quellen und Nachweise

ORD-Eintrag
ord-3eca32ec96e34b94909277e13a1f16e0
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420301

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