Reaktion #705661

Reaktionsgleichung

water

benzyl bromide

7-(1-adamantyl)-6-hydroxy-2-bromonaphthalene

sodium hydride

→

7-(1-adamantyl)-6-benzyloxy-2-bromonaphthalene

Lösungsmittel

ethanol

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirring
2. 2
   Extraktionextracted with ethyl ether
3. 3
   Sonstigethe organic phase was separated
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe residue obtained
7. 7
   Temperaturheated
8. 8
   Temperaturto reflux
9. 9
   Temperaturcooled
10. 10
    Filtrationfiltered
11. 11
    Sonstigedried
12. 12
    Sonstige12.5 g (80%) of the expected compound were collected

Vorschrift

1.26 g (42 mmol) of sodium hydride (80% in oil) and 50 ml of DMF were introduced into a 3-necked flask, a solution of 12.5 g (35 mmol) of 7-(1-adamantyl)-6-hydroxy-2-bromonaphthalene in 100 ml of DMF was added dropwise and stirring was carried out until gas evolution had ceased. 5 ml (42 mmol) of benzyl bromide were then added and stirring was carried out at room temperature for 2 hours. The reaction mixture was poured into water and extracted with ethyl ether and the organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue obtained was taken up in ethanol, heated to reflux, cooled, filtered and dried. 12.5 g (80%) of the expected compound were collected, which compound had a melting point of 150°-1° C.

Quelle