Reacción #91529

Ecuación de reacción

sodium pyrosulfite

aluminum chloride

bromine

bromine

1-adamantanecarboxylic acid

→

compound

Rendimiento 92.8%

3-bromo-adamantane-1-carboxylic acid

Rendimiento 92.8%

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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%).

Fuente