Iodine → 3-(2-Ethoxyphenyl)-3-hydroxy-5-iodoindol-2-one

HRID 219754

Reaktionsgleichung

Reaktionsgleichung von HRID 219754
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:10][CH3:11].II.[I:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=[O:24])[C:18]2=[O:25].[NH4+].[Cl-]>CCOCC.O1CCCC1>[CH2:10]([O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:18]1([OH:25])[C:17]2[C:21](=[CH:22][CH:23]=[C:15]([I:14])[CH:16]=2)[NH:20][C:19]1=[O:24])[CH3:11]

Komponenten

8

Edukt 5

HCID 807IodineHCID 25517Ammonium ChlorideHCID 685002-Bromophenetole2×HCID 886955-IodoisatinHCID 5462224Magnesium

Produkt 1

HCID 574664423-(2-Ethoxyphenyl)-3-hydroxy-5-iodoindol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

4 g (164 mMol) of magnesium turnings and 5% of the total amount of 2-bromo-1-ethoxybenzene were put into 20 ml of ether and, after addition of a little iodine, were heated until the reaction started. 33.1 g (165 mMol) of 2-bromo-1-ethoxybenzene dissolved in 100 ml of ether were slowly added dropwise to the boiling solution in such a way that the reaction continued with gentle boiling. Then, while cooling slightly to 20° C., 15 g (54.9 mMol) of 5-iodoisatin in 400 ml of anhydrous tetrahydrofuran were added dropwise. The mixture was then stirred at room temperature for 2 h. The reaction solution was poured into an aqueous NH4Cl solution with stirring. This aqueous phase was extracted several times with ethyl acetate, and the combined aqueous phase was washed four times with water, dried and concentrated in vacuo, resulting in the product as a crystalline precipitate. 19.2 g of the product were obtained.

Aufarbeitung

  1. temperaturewere heated until the reaction
  2. additionwere slowly added dropwise to the boiling solution in such a way that the reaction
  3. stirringwith stirring
  4. extractionThis aqueous phase was extracted several times with ethyl acetate
  5. washthe combined aqueous phase was washed four times with water
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customresulting in the product as a crystalline precipitate

Quellen und Nachweise

ORD-Eintrag
ord-f588b2f796754e5b9d1ed63240c9f62f
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202870B2

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