Water → 7-(1-Adamantyl)-6-benzyloxy-2-bromonaphthalene

HRID 618479

Reaktionsgleichung

Reaktionsgleichung von HRID 618479
[H-].[Na+].[C:3]12([C:13]3[CH:22]=[C:21]4[C:16]([CH:17]=[CH:18][C:19]([Br:23])=[CH:20]4)=[CH:15][C:14]=3[OH:24])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>CN(C=O)C.C(O)C>[C:3]12([C:13]3[CH:22]=[C:21]4[C:16]([CH:17]=[CH:18][C:19]([Br:23])=[CH:20]4)=[CH:15][C:14]=3[O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:10][CH:9]3[CH2:11][CH:5]([CH2:6][CH:7]([CH2:8]3)[CH2:12]1)[CH2:4]2

Komponenten

7

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 145490723-(Adamantan-1-yl)-6-bromonaphthalen-2-ol

Produkt 1

HCID 220003597-(1-Adamantyl)-6-benzyloxy-2-bromonaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  1. stirringstirring
  2. extractionextracted with ethyl ether
  3. customthe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. temperatureheated
  8. temperatureto reflux
  9. temperaturecooled
  10. filtrationfiltered
  11. customdried
  12. custom12.5 g (80%) of the expected compound were collected

Quellen und Nachweise

ORD-Eintrag
ord-3d5c682f50c74932bc97b777b9476532
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952382

Verknüpfte Notizen

Wird geladen…