4-Bromo-2,5-dimethyl-1h-indene → 2,5-Dimethyl-4-phenylindene

HRID 1372538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1372538
Br[C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:12])[CH2:6]2.[C:13]1([Mg]Br)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OCC)C.Cl[Ni](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:12][C:5]1[CH2:6][C:7]2[C:3]([CH:4]=1)=[C:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([CH3:11])=[CH:9][CH:8]=2

Komponenten

5

Edukt 2

HCID 231154544-Bromo-2,5-dimethyl-1h-indeneHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 231154562,5-Dimethyl-4-phenylindene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418751HCID 178418751, VerbindungKatalysatorHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

4-Bromo-2,5-dimethylindene (9.0 g, 40 mmol), prepared as described under I.(b) above, and NiCl2(PPh3)2 (1.8 g, 2.8 mmol) were dissolved in 300 ml of diethyl ether (Et2O). Phenylmagnesium bromide, 3.0 M in Et2O, (13.5 ml, 40 mmol) was added under vigorous stirring and the reaction stirred overnight at reflux. The resultant reaction was slowly quenched with H2O to neutralize unreacted Grignard reagent, subsequently treated with 100 ml of 10% HCl(aq), and neutralized with saturated sodium bicarbonate aqueous solution. The resultant organic layer was dried with magnesium sulfate, and the solvent was removed by rotary evaporation. The remaining residue was loaded onto a silica gel column and eluted with hexane. Yield is 1.3 g (15%).

Aufarbeitung

  1. stirringthe reaction stirred overnight
  2. temperatureat reflux
  3. customThe resultant reaction
  4. customwas slowly quenched with H2O
  5. additionsubsequently treated with 100 ml of 10% HCl(aq)
  6. dry with materialThe resultant organic layer was dried with magnesium sulfate
  7. customthe solvent was removed by rotary evaporation
  8. washeluted with hexane

Quellen und Nachweise

ORD-Eintrag
ord-521cbc1d20c3480697c10f38a8226be0
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157591B2

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