Reaktion #338894

Reaktionsgleichung

magnesium

5-(1-adamantyl)-2-bromotoluene

4-(1-adamantyl)-bromobenzene

hydrochloric acid

→

4,4′-di(1-adamantyl)-2-methyl-1,1′-biphenyl

Ausbeute 79.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere charged
2. 2
   Temperaturrefluxed under a nitrogen atmosphere for two hours
3. 3
   workup.ADDITIONwas added
4. 4
   Temperaturunder nitrogen flow and the mixture was refluxed for 12 hours
5. 5
   Temperaturthe mixture was refluxed for 30 minutes
6. 6
   SonstigeAfter an aqueous layer was separated
7. 7
   Sonstigeremoved
8. 8
   Waschenthe reaction solution was washed with 200 mL of saturated sodium hydrogencarbonate aqueous solution
9. 9
   Sonstigefollowed by removal of solvent under reduced pressure
10. 10
    SonstigeSolid thus obtained

Vorschrift

In a 1 L recovery flask, 3.19 g of magnesium (131 mmol), g of 5-(1-adamantyl)-2-bromotoluene (131 mmol), 200 mL of tetrahydrofuran and a stirrer were charged and refluxed under a nitrogen atmosphere for two hours to prepare a Grignard reagent. Next, in another 1 L recovery flask, 38.2 g of 4-(1-adamantyl)-bromobenzene (131 mmol), 9.19 mg of bis(triphenylphosphine)palladium dichloride (13.1 mmol), 300 mL of tetrahydrofuran and a stirrer were charged. A tetrahydrofuran solution, which is the above-prepared Grignard reagent, was added thereto under nitrogen flow and the mixture was refluxed for 12 hours. Then, 60 mL of 10% hydrochloric acid aqueous solution was added thereto and the mixture was refluxed for 30 minutes. After an aqueous layer was separated and removed therefrom, the reaction solution was washed with 200 mL of saturated sodium hydrogencarbonate aqueous solution, followed by removal of solvent under reduced pressure. Solid thus obtained was refined by alumina column chromatography, thus obtaining 45.1 g of 4,4′-di(1-adamantyl)-2-methyl-1,1′-biphenyl (103.5 mmol; yield: 79.0%).

Quelle