Ethyl 3-bromobenzoate → 6-Cyclopentyl-benzoic acid ethyl ester

HRID 334046

Reaktionsgleichung

Reaktionsgleichung von HRID 334046
Br[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br-].[CH:14]1([Zn+])[CH2:18][CH2:17][CH2:16][CH2:15]1>C1COCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:8]([O:7][C:5](=[O:6])[C:4]1[C:10]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:11][CH:12]=[CH:2][CH:3]=1)[CH3:9]

Komponenten

6

Edukt 2

HCID 90488Ethyl 3-bromobenzoateHCID 178419768HCID 178419768, Verbindung

Produkt 1

HCID 866882776-Cyclopentyl-benzoic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To 1.00 mL (6.24 mmol) ethyl 3-bromobenzoate was added 13.0 mL (6.50 mmol) 0.5 M cyclopentylzinc bromide solution in THF followed by 100 mg (0.137 mmol) 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) under argon atmosphere. The reaction mixture was stirred at 85° C. for 1.5 h, then diluted with water and stirred at RT for 12 h. The suspension was extracted with EtOAc. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was filtered through Alox (EtOAC) and concentrated in vacuo.

Aufarbeitung

  1. stirringstirred at RT for 12 h
  2. extractionThe suspension was extracted with EtOAc
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationThe crude material was filtered through Alox (EtOAC)
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-592a1af4737c4ee3975dbeaebcb1cea7
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883789B2

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