Reaction equation
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].[CH:17]([C:19]1[CH:24]=[CH:23][C:22](OB(O)O)=[CH:21][CH:20]=1)=[O:18]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:22]2[CH:23]=[CH:24][C:19]([CH:17]=[O:18])=[CH:20][CH:21]=2)[CH:5]=[C:6]([F:9])[C:7]=1[F:8]Participants
Conditions
- Temperature
- 60 °C
Procedure
In a nitrogen atmosphere, a solution prepared by mixing 15.00 g of 3,4,5-trifluorobromobenzene, 0.25 g of tetrakis-triphenylphosphine palladium, 30 mL of an aqueous potassium carbonate solution (2 mol/L), and 75 mL of THF was heated to 60° C., and 10.71 g of 4-formylphenylboric acid was added to the solution over 20 minutes. After the resultant mixture was stirred at 60° C. for 3 hours, the mixture was allowed to cool, and an organic layer was separated by adding hexane. The organic layer was washed with saturated brine and dried by adding sodium sulfate, and then the solvent was distilled off under reduced pressure. As a result of purification by silica gel column chromatography, 14.77 g of 4-(3,4,5-trifluorophenyl)benzaldehyde was yielded.
Workup
- customIn a nitrogen atmosphere, a solution prepared
- temperatureto cool
- customan organic layer was separated
- additionby adding hexane
- washThe organic layer was washed with saturated brine
- customdried
- additionby adding sodium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customAs a result of purification by silica gel column chromatography
Sources & evidence
- ORD record
- ord-1f4bff464cbe48f4820367ccdde28900
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916718B2
Linked notes
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