Reaktion #12061

Reaktionsgleichung

bromo-methyl-cyclohexane

magnesium

2-bromo-indene

bromo-methyl-cyclohexane

→

2-(cyclohexylmethyl)indene

Lösungsmittel

ether

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was heated
2. 2
   Temperaturto reflux
3. 3
   workup.ADDITIONan additional 150 mg of freshly ground Mg was added and after 5 hours
4. 4
   TemperaturThe system was gently heated
5. 5
   Temperaturto reflux overnight
6. 6
   Temperaturcooled
7. 7
   Sonstigequenched
8. 8
   workup.ADDITIONby adding 150 mL of 1.0 M aqueous hydrochloric acid
9. 9
   SonstigeThe product was isolated
10. 10
    Sonstigepurified (hexanes/silica) as for 2-benzyl-indene

Vorschrift

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.

Quelle