Reaktion #95972

Reaktionsgleichung

1-ethyladamantane

1-ethyladamantane

bromine

→

1-bromo-3-ethyladamantane

Ausbeute 90.3%

Lösungsmittel

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturover which time the temperature was increased
2. 2
   Temperaturto reflux
3. 3
   SonstigeThe heat was removed
4. 4
   Temperaturafter cooling
5. 5
   workup.ADDITIONa 40 ml portion of carbon tetrachloride was added
6. 6
   workup.ADDITIONThe mixture was poured into 120 ml of ice water and enough solid sodium sulfite
7. 7
   workup.ADDITIONwas added
8. 8
   Sonstigeto destroy the excess bromine
9. 9
   SonstigeThe layers were separated
10. 10
    Extraktionthe aqueous phase was extracted with three portions of carbon tetrachloride
11. 11
    WaschenThe combined extracts were washed with water
12. 12
    Trocknen5% aqueous sodium bicarbonate solution, then dried over magnesium sulfate (anhydrous)
13. 13
    SonstigeEvaporation of solvent
14. 14
    Sonstigeyielded a yellow liquid which
15. 15
    workup.DISTILLATIONwas distilled

Vorschrift

1-Bromo-3-ethyladamantane was prepared from 1-ethyladamantane (K. Gerzon et al, J. Med. Chem., 6, 760, 1963) by stirring 0.944 grams (5.76 mmol) of 1-ethyladamantane with 10 ml of liquid bromine for 4 hours, over which time the temperature was increased to reflux. The heat was removed and after cooling, a 40 ml portion of carbon tetrachloride was added. The mixture was poured into 120 ml of ice water and enough solid sodium sulfite was added with stirring to destroy the excess bromine. The layers were separated and the aqueous phase was extracted with three portions of carbon tetrachloride. The combined extracts were washed with water, then 5% aqueous sodium bicarbonate solution, then dried over magnesium sulfate (anhydrous). Evaporation of solvent yielded a yellow liquid which was distilled to afford 1.263 grams (90.3%) of 1-bromo-3-ethyladamantane, bp 114°-115° C. (3.5 mm).

Quelle