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

Benzaldehyde → 2,4-Di(prop-1-en-2-yl)dibenzo[b,d]thiophen-3-amine

HRID 1750926
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1750926
Br[C:2]1[C:14]([NH2:15])=[C:13](Br)[C:5]2[S:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[CH3:17][C:18]1(C)[C:22](C)(C)OB(C(C)=C)O1.[CH:29](=O)[C:30]1C=CC=C[CH:31]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C1(C)C=CC=CC=1>[CH2:17]=[C:18]([C:2]1[C:14]([NH2:15])=[C:13]([C:30]([CH3:31])=[CH2:29])[C:5]2[S:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1)[CH3:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 240BenzaldehydeHCID 62657Potassium Phosphate, TribasicHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 584010402,4-Dibromodibenzo[b,d]thiophen-3-amine

Produkt 1

HCID 584009962,4-Di(prop-1-en-2-yl)dibenzo[b,d]thiophen-3-amineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a degassed toluene (200 mL), 2,4-dibromodibenzo[b,d]thiophen-3-amine (12.15 g, 34.0 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (17.15 g, 102 mmol), benzaldehyde (3.61 g, 34.0 mmol), potassium phosphate (23.51 g, 102 mmol) dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (1.676 g, 4.08 mmol) and Pd2(dba)3 (0.935 g, 1.021 mmol) and water (20 mL) were sequentially added. The solution was refluxed for overnight in an atmosphere of nitrogen and then allowed to cool to room temperature. The reaction was diluted with ethyl acetate and the organic phase was separated from the aqueous phase. The organic phase was dried over sodium sulfate and the solvent was removed under vacuum. The product was chromatographed using silica gel with ethylacetate and hexanes as the eluent. The solvent was removed to give the title compound (9.0, 95%).

Aufarbeitung

  1. temperatureThe solution was refluxed for overnight in an atmosphere of nitrogen
  2. customthe organic phase was separated from the aqueous phase
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customthe solvent was removed under vacuum
  5. customThe product was chromatographed
  6. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-03171f66983c42f68f9f6cbdfa382131
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09156870B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion