Reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5]Br.[C:7]12([C:17]([OH:19])=[O:18])[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>>[Br:5][C:9]12[CH2:15][CH:13]3[CH2:12][CH:11]([CH2:16][C:7]([C:17]([OH:19])=[O:18])([CH2:14]3)[CH2:8]1)[CH2:10]2Participants
Conditions
- Temperature
- -5 °C
Procedure
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%).
Workup
- stirringby stirring for 1 hour
- temperaturewith maintaining the temperature at −5° C
- stirringThe reaction mixture was then additionally stirred for 48 hours
- temperaturewith raising the temperature slowly to room temperature
- stirringUpon completion of stirring
- customto terminate
- customthe reaction
- extractionThe de-colored reactant was extracted
- dry with materialThe extracted organic layer was dried over sodium sulfate
- concentrationfollowed by concentration under reduced pressure
Sources & evidence
- ORD record
- ord-adc2ba3d385e494b94f6a36ac18a0cc8
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447063B2
Linked notes
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