StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

p-Bromochlorobenzene → HCID 67501835, Verbindung

HRID 1187761
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1187761
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=[CH:19][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7806p-BromochlorobenzeneHCID 10796Cesium carbonateHCID 66705807HCID 66705807, Verbindung

Produkt 1

HCID 67501835HCID 67501835, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

In a pressure tube, (S)-4-[2-(4-amino-phenyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.3 g), 1-bromo-4-chlorobenzene (215 mg) and cesium carbonate (458 mg) were combined with dioxane (3 ml) to give a yellow suspension. The mixture was degassed by bubbling through argon for several minutes. Xantphos (32.5 mg) and tris(dibenzylideneacetone)dipalladium chloroform complex (29.1 mg) were then added and the tube was sealed. The reaction mixture was stirred at 110° C. overnight. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was purified by flash chromatography (SiO2; gradient: 0% to 100% EtOAc in hexane) to afford (S)-4-{2-[4-(4-chloro-phenylamino)-phenyl]-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (228 mg, 57%) as a yellow oil. MS (EI): 432 ({37Cl}M+), 430 ({35Cl}M+H—OH+), 376 ({37Cl}[M−C4H8]+), 374 ({35Cl}[M−C4H8]), 231 ({37Cl}[ClC6H4NHC6H4CH═CH2]+), 229 ({35Cl}[ClC6H4NHC6H4CH═CH2]+), 57 ([C4H9]+).

Aufarbeitung

  1. customto give a yellow suspension
  2. customThe mixture was degassed
  3. customby bubbling through argon for several minutes
  4. additionXantphos (32.5 mg) and tris(dibenzylideneacetone)dipalladium chloroform complex (29.1 mg) were then added
  5. customthe tube was sealed
  6. temperatureThe reaction mixture was then cooled to room temperature
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (SiO2; gradient: 0% to 100% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0df10265f8e74cfab65efee015e1cb24
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08673950B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion