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Trifluoroacetic acid → 5-bromo-6-fluoro-2,3-dihydro-1H-indole-7-carboxylic acid

HRID 656066
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 656066
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:12]([OH:14])=[O:13])[C:10]=1[F:11])[N:7](C(OC(C)(C)C)=O)[CH2:6][CH2:5]2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:12]([OH:14])=[O:13])[C:10]=1[F:11])[NH:7][CH2:6][CH2:5]2
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Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 593326855-Bromo-1-{[(1,1-dimethylethyl)oxy]carbonyl}-6-fluoro-2,3-dihydro-1H-indole-7-carboxylic acid

Produkt 1

HCID 593326645-bromo-6-fluoro-2,3-dihydro-1H-indole-7-carboxylic acidAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-bromo-1-{[(1,1-dimethylethyl)oxy]carbonyl}-6-fluoro-2,3-dihydro-1H-indole-7-carboxylic acid (8.3 g, 0.023 mol) in DCM (90 mL) was added TFA (90 mL). The reaction mixture was stirred at room temperature for 3 h and then concentrated. The residue was partitioned between EtOAc (100 mL) and water (100 mL), and the aqueous fraction was extracted with EtOAc (2×50 mL). The combined organic layers were washed with water (1×50 mL) and brine (1×50 mL). dried (Na2SO4) and concentrated under reduced pressure, giving 5.9 g (99%) of the title compound.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue was partitioned between EtOAc (100 mL) and water (100 mL)
  3. extractionthe aqueous fraction was extracted with EtOAc (2×50 mL)
  4. washThe combined organic layers were washed with water (1×50 mL) and brine (1×50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-518d7000c8e54c8cbdb3ceb2e9b3e25e
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08071584B2

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