2,5-Dichloronitrobenzene → 3-(4-Chloro-2-nitro-phenoxy)-cyclopentanecarboxylic acid ethyl ester

HRID 1773525Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1773525
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([O:14][C:15]([CH:17]1[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18]1)=[O:16])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>ClCCl>[CH2:12]([O:14][C:15]([CH:17]1[CH2:21][CH2:20][CH:19]([O:22][C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[CH2:18]1)=[O:16])[CH3:13]

Komponenten

6

Edukt 4

HCID 69772,5-DichloronitrobenzeneHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 53407781Ethyl 3-hydroxycyclopentanecarboxylate

Produkt 1

HCID 580562213-(4-Chloro-2-nitro-phenoxy)-cyclopentanecarboxylic acid ethyl esterAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 1,4-dichloro-2-nitro-benzene (190 mg, 1.1 mmol), 3-hydroxy-cyclopentanecarboxylic acid ethyl ester (180 mg, 1.14 mmol), triphenylphosphine (448 mg) and DIAD (345 mg) in dichloromethane (10 mL) was stirred at room temperature overnight. The reaction mixture was then evaporated under reduced pressure and the crude residue was purified by flash chromatography to afford 280 mg of 3-(4-chloro-2-nitro-phenoxy)-cyclopentanecarboxylic acid ethyl ester.

Aufarbeitung

  1. customThe reaction mixture was then evaporated under reduced pressure
  2. customthe crude residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7e3ddfa5dd90428e9fce5a23ea53e54b
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255110B2

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