Ethyl diazoacetate → Ethyl 2-(bromomethyl)-3-(3-nitrophenyl)cyclopropane Carboxylate

HRID 1826417Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1826417
[Br:1][CH2:2]/[CH:3]=[CH:4]/[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1.[N+](=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N-]>ClCCl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[Br:1][CH2:2][CH:3]1[CH:4]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=2)[CH:16]1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Komponenten

5

Edukt 2

HCID 12192Ethyl diazoacetateHCID 58409941-[(E)-3-bromo-1-propenyl]-3-nitrobenzene

Produkt 1

HCID 22141287Ethyl 2-(bromomethyl)-3-(3-nitrophenyl)cyclopropane CarboxylateAusbeute 7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 423677Acetic acid, rhodium salt (4:2)KatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 1-[(E)-3-bromo-1-propenyl]-3-nitrobenzene (Preparation 22, 820 mg, 3.23 mmol) in dichloromethane (3 ml) was added rhodium (II) acetate dimer (20 mg, 0.046 mmol). To the mixture was added dropwise at room temperature over 3 h a solution of ethyl diazoacetate (0.47 ml, 510 mg, 4.47 mmol) in dichloromethane (3 ml), then the mixture was stirred at room temperature for 66 h. The mixture was purified by silica (100 g) column chromatography eluting with hexane:dichloromethane 100:0 to 50:50. Product containing fractions were combined and concentrated in vacuo to afford the title compound as a colourless oil (65 mg, 7%).

Aufarbeitung

  1. customThe mixture was purified by silica (100 g) column chromatography
  2. washeluting with hexane:dichloromethane 100:0 to 50:50
  3. additionProduct containing fractions
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2c956626e6e0440e8bc251c0b37d233b
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07049444B2

Notizen zur Reaktion

Wird geladen…