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Phthalimide → 2-(2,2-difluoroethyl)-1H-isoindole-1,3(2H)-dione

HRID 2040921
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2040921
[F:1][CH:2]([F:5])[CH2:3]Cl.[C:6]1(=[O:16])[NH:10][C:9](=[O:11])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]12.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[F:1][CH:2]([F:5])[CH2:3][N:10]1[C:6](=[O:16])[C:7]2[C:8](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:9]1=[O:11]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 2736499Chlorodifluoroethane (mixed isomers)

Produkt 1

HCID 866684402-(2,2-difluoroethyl)-1H-isoindole-1,3(2H)-dioneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysator
HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

An amount of 27.6 g (0.269 mol) of 2,2-difluoro-1-chloroethane, 2.16 g (6.73 mmol) of tetra(n-butyl)ammonium bromide and 20 g (0.135 mol) of phthalimide are dissolved in 95 g of N,N-dimethylformamide and treated with 46.96 g (0.336 mol) of potassium carbonate. The reaction mixture is stirred in an autoclave under pressure at 120° C. for 16 h. After the end of the reaction, cooling is carried out to ambient temperature and the solvent is exhaustively removed under vacuum. The remaining residue is treated with 150 ml of water and the solid is filtered off. The filter residue is washed twice with water and the product is dried under vacuum. An amount of 28.5 g of 2-(2,2-difluoroethyl)-1H-isoindole-1,3(2H)-dione with a purity of 97.4% is obtained. This corresponds to a yield of 97.7% of theory.

Aufarbeitung

  1. customAfter the end of the reaction
  2. temperaturecooling
  3. customis carried out to ambient temperature
  4. customthe solvent is exhaustively removed under vacuum
  5. additionThe remaining residue is treated with 150 ml of water
  6. filtrationthe solid is filtered off
  7. washThe filter residue is washed twice with water
  8. customthe product is dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-93240e026dcf4615aff1ef2b5f0ec7b9
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08580973B2

Notizen zur Reaktion

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