Water → 1-(Cyclopentyloxy)-2-iodobenzene

HRID 53487

Reaktionsgleichung

Reaktionsgleichung von HRID 53487
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].[Br-].Br[CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.O>CN(C)C=O.C(OCC)(=O)C>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 107842-IodophenolHCID 11430Potassium CarbonateHCID 199598491-Bromocyclopentane bromide

Produkt 1

HCID 153433181-(Cyclopentyloxy)-2-iodobenzeneAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 2-iodophenol (8.0 g, 36.4 mmol), milled potassium carbonate (5.5 g, 39.9 mmol, 1.1 eq) and 1-bromocyclopentane bromide (3.9 ml, 36.4 mmol) in 25 ml of N,N-dimethylformamide was heated at 120° C. for 1.1 hrs and cooled. The mixture was poured into water and extracted twice with ether. The ether layer was dried over magnesium sulfate, filtered, and concentrated to give an oil. The crude product was dissolved in ethyl acetate and filtered through a short pad of silica gel. The filtrate was redried over magnesium sulfate, filtered and concentrated under vacuum to give 10 g (95%) of product as an oil.

Aufarbeitung

  1. temperaturecooled
  2. extractionextracted twice with ether
  3. dry with materialThe ether layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oil
  7. filtrationfiltered through a short pad of silica gel
  8. dry with materialThe filtrate was redried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-50bf3e7503df46bfaa8dd67ddc157eac
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05620677

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