4-Chloro-2-methyl-1H-indene → 4-(3',5'-Di-t-butylphenyl)-2-methylindene

HRID 842470

Reaktionsgleichung

Reaktionsgleichung von HRID 842470
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:11])[CH2:6]2.[C:12]([C:16]1[CH:17]=[C:18]([Mg]Br)[CH:19]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:21]=1)([CH3:15])([CH3:14])[CH3:13]>CCOCC.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>[C:12]([C:16]1[CH:17]=[C:18]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH:4]=[C:5]([CH3:11])[CH2:6]3)[CH:19]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:21]=1)([CH3:15])([CH3:14])[CH3:13]

Komponenten

5

Edukt 2

HCID 120107424-Chloro-2-methyl-1H-indeneHCID 178441125HCID 178441125, Verbindung

Produkt 1

HCID 120107434-(3',5'-Di-t-butylphenyl)-2-methylindene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418751HCID 178418751, VerbindungKatalysatorHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

4-Chloro-2-methylindene (6.1 g, 37 mmol) and NiCl2(PPh3)2 (1.8 g, 2.8 mmol) were dissolved in 150 mL of Et2O. 3,5-Di-t-butylphenylmagnesium bromide (10 g, 37 mmol) as a Et2O solution was added to the solution and the reaction was stirred overnight at room temperature. After overnight stirring, the reaction was slowly quenched with H2O to neutralize unreacted Grignard. The solution was subsequently treated with 100 mL of 10% HCl(aq), neutralized with saturated sodium bicarbonate aqueous solution. The 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 was 4.6 g (40%).

Aufarbeitung

  1. stirringAfter overnight stirring
  2. customthe reaction was slowly quenched with H2O
  3. additionThe solution was subsequently treated with 100 mL of 10% HCl(aq)
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. customthe solvent was removed by rotary evaporation
  6. washeluted with hexane

Quellen und Nachweise

ORD-Eintrag
ord-59a32edaf34e412e8c6e8638452f9be8
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06376411B1

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