Iodine → HCID 23293626, Verbindung

HRID 362807Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 362807
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].II>C(OCC)C.C1C=CC=CC=1.[Zn]>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[OH:11])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 807IodineHCID 7748Ethyl bromoacetateHCID 15194646-Fluoro-1-indanone

Produkt 1

HCID 23293626HCID 23293626, VerbindungAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 22174802Benzene etherLösungsmittel

Versuchsvorschrift

A mixture of 6-fluoro-1-indanone (5.0 g, 33.3 mmol), ethyl bromoacetate (8.3 g, 50.0 mmol, Aldrich), activated zinc powder (3.2 g, 50.0 mmol, Mallinckrodt; Org. Synth., Coll. Vol. 6, 290, 1988) and a few crystals of iodine in diethyl ether-benzene (1:1, 100 mL) was heated at reflux under nitrogen for 24 h. The mixture was filtered and the filtrate was concentrated in vacuo. The residue in diethyl ether was vigorously stirred with excess dilute ammonium hydroxide, dried and concentrated to give ethyl 2-(6-fluoro-1-hydroxy-1-indanyl)acetate as an amber oil (7.6 g, 97%);

Aufarbeitung

  1. temperatureat reflux under nitrogen for 24 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customdried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dda5f779c25b4300b810346cbc832ce2
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872118

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