Reaktion #91529

Reaktionsgleichung

sodium pyrosulfite

aluminum chloride

bromine

bromine

1-adamantanecarboxylic acid

→

compound

Ausbeute 92.8%

3-bromo-adamantane-1-carboxylic acid

Ausbeute 92.8%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGby stirring for 1 hour
2. 2
   Temperaturwith maintaining the temperature at −5° C
3. 3
   workup.STIRRINGThe reaction mixture was then additionally stirred for 48 hours
4. 4
   Temperaturwith raising the temperature slowly to room temperature
5. 5
   workup.STIRRINGUpon completion of stirring
6. 6
   Sonstigeto terminate
7. 7
   Sonstigethe reaction
8. 8
   ExtraktionThe de-colored reactant was extracted
9. 9
   TrocknenThe extracted organic layer was dried over sodium sulfate
10. 10
    Einengenfollowed by concentration under reduced pressure

Vorschrift

A two-neck round bottom flask was connected to a reflux condenser, to which aluminum chloride (AlCl3, 7.15 mmol) was injected, followed by cooling at −5° C. in argon environment. Then, bromine (Br2, 66 mmol) was added thereto, followed by stirring for 15 minutes. 1-adamantanecarboxylic acid (5.5 mmol) was added to the reaction mixture at a time, followed by stirring for 1 hour with maintaining the temperature at −5° C. The reaction mixture was then additionally stirred for 48 hours with raising the temperature slowly to room temperature. Upon completion of stirring, ice water was poured to the mixture to terminate the reaction. Excessive bromine was de-colored by adding sodium pyrosulfite. The de-colored reactant was extracted by using chloroform. The extracted organic layer was dried over sodium sulfate, followed by concentration under reduced pressure to give the target compound (5.016 mmol, 92.83%).

Quelle