1H-Indene, 2-bromo- → 2-(Cyclohexylmethyl)indene

HRID 11965

Reaktionsgleichung

Reaktionsgleichung von HRID 11965
[Mg].Br[C:3]1([CH3:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Br[C:11]1[CH2:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2>CCOCC.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH:3]1([CH2:9][C:11]2[CH2:19][C:18]3[C:13]([CH:12]=2)=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Komponenten

6

Edukt 3

HCID 5755861H-Indene, 2-bromo-HCID 5462224MagnesiumHCID 125021291-Bromo-1-methylcyclohexane2×

Produkt 1

HCID 219770202-(Cyclohexylmethyl)indene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418745HCID 178418745, VerbindungKatalysatorHCID 3283Diethyl EtherLösungsmittel3×

Versuchsvorschrift

To a suspension of freshly ground magnesium turnings (0.40 g, 16 mmol) in 100 mL of ether was added about 20 percent of a 100 ml ether solution containing 2.5 g (14 mmol) of bromo-methyl-cyclohexane. The reaction was heated to reflux and the remaining bromo-methyl-cyclohexane solution added over one hour. After 1 hour, an additional 150 mg of freshly ground Mg was added and after 5 hours, the mixture was cooled to room temperature. The Grignard solution was added over one hour to a mixture of 2.45 g (13 mmol) of 2-bromo-indene, 100 mg of NiCl2(dppp) (0.15 mmol) and 100 mL of ether. The system was gently heated to reflux overnight and then cooled and quenched by adding 150 mL of 1.0 M aqueous hydrochloric acid. The product was isolated and purified (hexanes/silica) as for 2-benzyl-indene.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. additionan additional 150 mg of freshly ground Mg was added and after 5 hours
  4. temperatureThe system was gently heated
  5. temperatureto reflux overnight
  6. temperaturecooled
  7. customquenched
  8. additionby adding 150 mL of 1.0 M aqueous hydrochloric acid
  9. customThe product was isolated
  10. custompurified (hexanes/silica) as for 2-benzyl-indene

Quellen und Nachweise

ORD-Eintrag
ord-a0aff5b67a1741c1bd8e8bebd2cdd783
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098356B2

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