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

Styrene → HCID 73990325, Verbindung

HRID 2416407
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2416407
Br[C:2]1[CH:7]=[CH:6][C:5]([Si:8]([C:23]2[CH:28]=[CH:27][C:26](Br)=[CH:25][CH:24]=2)([C:16]2[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=2)[C:9]2[CH:14]=[CH:13][C:12](Br)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH2:30]=[CH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C([O-])([O-])=O.[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CC([O-])=O.CC([O-])=O.[Pd+2].CC(N(C)C)=O>[C:6]1([CH:30]=[CH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:7]=[CH:2][CH:3]=[CH:4][C:5]=1[Si:8]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH:30]=[CH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH:30]=[CH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:30]=[CH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 7501StyreneHCID 11430Potassium CarbonateHCID 12729346Tetrakis(4-bromophenyl)silane

Produkt 1

HCID 73990325HCID 73990325, VerbindungAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysator
HCID 167845
palladium(II) acetate
Katalysator
HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A round bottom flask (50 mL) equipped with a teflon coated stir bar was charged with tetrakis(4-bromophenyl)silane (326 mg, 0.5 mmol), styrene (2.0 g, 12 mmol), Pd(OAc)2 (14 mg, 12 mol %), K2CO3 (690 mg, 5 mmol), n-Bu4NBr (645 mg, 2 mmol), and DMA (10 mL). The flask was fitted with a rubber septum and purged with nitrogen prior to heating (80° C.) with stirring for 48 hours. The reaction mixture was allowed to cool to room temperature, diluted with CH2Cl2, and washed five times with brine. The organic phase was dried with MgSO4, filtered through silica gel and the solvent was evaporated under reduced pressure. The residue was dissolved in CHCl3 and precipitated with hexanes. The colorless needle-like crystals were collected (52% yield). 1H NMR (CDCl3): δ 7.61 (d, J=8.0 Hz, 8H), 7.55 (m, 16H), 7.38 (t, J=7.3 Hz, J=8.0 Hz, 8H), 7.29 (t, J=7.3 Hz, 4H), 7.17 (AA′BB′ pattern, J=16.4 Hz, 8H). 13C NMR (CDCl3) δ 138.5, 137.1, 136.7, 133.4, 129.5, 128.6, 128.4, 127.7,126.5, 125.9.

Aufarbeitung

  1. customA round bottom flask (50 mL) equipped with a teflon coated stir bar
  2. customThe flask was fitted with a rubber septum
  3. custompurged with nitrogen
  4. temperatureto cool to room temperature
  5. additiondiluted with CH2Cl2
  6. washwashed five times with brine
  7. dry with materialThe organic phase was dried with MgSO4
  8. filtrationfiltered through silica gel
  9. customthe solvent was evaporated under reduced pressure
  10. dissolutionThe residue was dissolved in CHCl3
  11. customprecipitated with hexanes
  12. customThe colorless needle-like crystals were collected (52% yield)

Quellen und Nachweise

ORD-Eintrag
ord-7c03add6e97b46ae8a799d029dcc5bea
Quelldatensatz
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06824890B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion