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1-Bromo-3-chloropropane → 5-Chloro-2-(4-chlorophenyl)pentanoic acid

HRID 1009434
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1009434
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C([Li])CCC.Br[CH2:18][CH2:19][CH2:20][Cl:21].C(OCC)(=O)C>C1COCC1>[Cl:21][CH2:20][CH2:19][CH2:18][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C:9]([OH:11])=[O:10]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 80061-Bromo-3-chloropropaneHCID 8857Ethyl AcetateHCID 15880(4-Chlorophenyl)acetic acidHCID 178418339Butyllithium

Produkt 1

HCID 670673305-Chloro-2-(4-chlorophenyl)pentanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of 4-chlorophenylacetic acid (1 g) in THF (30 mL) was stirred at −78° C. for 20 minutes. n-Butyl lithium (2.66 M solution in hexane, 4.41 mL) was added to the solution, and the reaction solution was stirred at −78° C. for one hour. Thereafter, the reaction solution was stirred at 0° C. for one hour, 1-bromo-3-chloropropane (0.638 mL) was added to the reaction solution, and the reaction solution was stirred at room temperature for 18 hours. Thereafter, ethyl acetate and 1 N aqueous 2hydrochloric acid were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 1.55 g of the title compound. The property values of the compound are as follows.

Aufarbeitung

  1. stirringThereafter, the reaction solution was stirred at 0° C. for one hour
  2. stirringthe reaction solution was stirred at room temperature for 18 hours
  3. customthe organic layer was separated
  4. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1ee92c0df31e4d80a5e3c7c6eeed1534
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07973033B2

Notizen zur Reaktion

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