반응 #91529

반응 방정식

sodium pyrosulfite

aluminum chloride

bromine

bromine

1-adamantanecarboxylic acid

→

compound

수율 92.8%

3-bromo-adamantane-1-carboxylic acid

수율 92.8%

반응 조건

후처리

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

실험 절차

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%).

출처