Bromoethene → 1-Ethynyladamantane

HRID 231928

Reaktionsgleichung

Reaktionsgleichung von HRID 231928
Br[CH:2](Br)[CH2:3][C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH2:7]3)[CH2:5]1)[CH2:11]2.C=CBr.CC(C)([O-])C.[K+]>COCCOCCOCCOC.O>[C:3]([C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH2:7]3)[CH2:5]1)[CH2:11]2)#[CH:2]

Komponenten

6

Edukt 3

HCID 11641BromoetheneHCID 137375171-(2,2-Dibromoethyl)adamantaneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 5947811-Ethynyladamantane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8189TriglymeLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A solution of 45 g (0.17 mol) of 1-bromoadamantane in 60 ml of vinyl bromide was cooled to -65° C. and 10 g of aluminum bromide was added portionwise over 2 h. The mixture was then poured on to 500 g of ice, neutralized with 10% aqueous sodium carbonate solution, and extracted with 3×100 ml of methylene chloride. The combined extracts were dried (MgSO4) and evaporated to yield 70 g of an oil containing 1-(2,2-dibromoethyl)adamantane and polyvinyl bromide (NMR). This oil was dissolved in 100 ml of triglyme, 38 g (0.34 mol) of potassium t-butoxide added, nd the mixture heated at 160° C. for 3 h. The mixture was cooled, diluted with 300 ml of water and extracted with 3×100 ml of hexane. The combined hexane extracts were dried (MgSO4) , and distilled to give 12 g (52% based on 1-bromoadamantane) of 1 -ethynyladamantane: mp 82°-83° C.; bp 95-100 (l mm); NMR δ1.9-2.6 ppm.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. extractionextracted with 3×100 ml of hexane
  3. dry with materialThe combined hexane extracts were dried (MgSO4)
  4. distillationdistilled
  5. customto give 12 g (52% based on 1-bromoadamantane) of 1 -ethynyladamantane

Quellen und Nachweise

ORD-Eintrag
ord-a292e6886afb4bf2aee298b476519b79
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04849565

Verknüpfte Notizen

Wird geladen…