Trifluoroacetic acid → 4-fluoro-2,3-dihydro-1H-isoindol-1-one

HRID 877234Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877234
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4](O)[NH:5][C:6]2=[O:11].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:11]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 668996124-fluoro-3-hydroxy-2,3-dihydro-1H-isoindol-1-one

Produkt 1

HCID 220646804-fluoro-2,3-dihydro-1H-isoindol-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4.05 g (about 24.2 mmol) of 4-fluoro-3-hydroxy-2,3-dihydro-1H-isoindol-1-one were initially charged in 10 ml of dichloromethane, 22.4 ml (290.8 mmol) of trifluoroacetic acid and 7.7 ml (48.5 mmol) of triethylsilane were added and the mixture was stirred at RT overnight. The reaction mixture was then concentrated and the residue was dissolved in dichloromethane and washed with sodium bicarbonate solution. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 3:1 to 1:1). This gave 890 mg (24.2% of theory) of the target compound.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with sodium bicarbonate solution
  4. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 3:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-c14164ba6d434abdb9d050b4df5652f5
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987256B2

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