Hydrochloric Acid → Ethyl 1-(4-bromophenyl)cyclopentane-1-carboxylate

HRID 2391064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2391064
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][CH2:20]Br.Cl>CN(C=O)C.CCOC(C)=O>[CH2:12]([O:11][C:9]([C:8]1([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:10])[CH3:13]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 7020609Ethyl 2-(4-bromophenyl)acetate

Produkt 1

HCID 66660571Ethyl 1-(4-bromophenyl)cyclopentane-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-bromophenylacetate (2 g, 8.2 mmol) in DMF (20 mL) at 0° C. was added sodium hydride (60% in mineral oil; 0.72 g, 18.1 mmol), and the mixture was stirred for 10 minutes. 1,4-Dibromobutane (1.07 mL, 9.0 mmol) was added, and the reaction was stirred at room temperature for 30 minutes. Once no starting material was seen by analytical tlc, the mixture was worked up with EtOAc and aqueous 10% HCl, and the crude material was purified by silica gel chromatography to give the title compound.

Aufarbeitung

  1. stirringthe reaction was stirred at room temperature for 30 minutes
  2. customthe crude material was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8604a3d5190d4b1ca22e518064c25665
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273780B2

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