Iodine → HCID 68681813, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[Mg].II.[N:15]1[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][CH:16]=1.[Cl-].[NH4+]>C1COCC1>[F:9][C:8]([C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=1[C:18]1([CH2:21][OH:22])[CH:17]=[CH:16][N:15]=[CH:20][CH2:19]1)([F:11])[F:10]Participants
Conditions
- Temperature
- 0 °C
Procedure
A solution of 4-bromobenzotrifluoride in 62 mL of THF was carefully added to a mixture of 1.9 grams (0.079 mole) of magnesium turnings and an iodine crystal (catalyst), during a period of 60 minutes while maintaining the reaction mixture at a temperature of no higher than 40° C. After this time, the reaction mixture was stirred and a solution of 5.0 grams (0.047 mole) of 4-pyridinecarboxaldehyde in 45 mL of THF was added dropwise. Upon completion of addition, the reaction mixture was stirred at ambient temperature for about 16 hours. The reaction mixture was then cooled to 0° C. and a sufficient amount of an aqueous solution saturated with ammonium chloride was added to quench the reaction. The mixture was then extracted with ethyl acetate, and the extract was washed with an aqueous solution saturated with sodium chloride. The extract was dried with sodium sulfate, filtered, and concentrated under reduced pressure, yielding about 15.2 grams of crude product.
Workup
- additionUpon completion of addition
- stirringthe reaction mixture was stirred at ambient temperature for about 16 hours
- customto quench
- customthe reaction
- extractionThe mixture was then extracted with ethyl acetate
- washthe extract was washed with an aqueous solution saturated with sodium chloride
- dry with materialThe extract was dried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-f98ec621862741df9678bb80fb2cda68
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07683070B2
Reaction notes
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