Potassium Phosphate, Tribasic → 4-Ethoxy-2',3',4'-trifluoro-5-methyl-[1,1'-biphenyl]-2-carbaldehyde
Reaction equation
Br[C:2]1[CH:9]=[C:8]([CH3:10])[C:7]([O:11][CH2:12][CH3:13])=[CH:6][C:3]=1[CH:4]=[O:5].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:51][C:52]1[C:57]([F:58])=[C:56]([F:59])[CH:55]=[CH:54][C:53]=1B(O)O>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:12]([O:11][C:7]1[CH:6]=[C:3]([CH:4]=[O:5])[C:2]([C:55]2[CH:54]=[CH:53][C:52]([F:51])=[C:57]([F:58])[C:56]=2[F:59])=[CH:9][C:8]=1[CH3:10])[CH3:13]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
To a degassed solution of 2-bromo-5-ethoxy-4-methylbenzaldehyde (300 mg, 1.31 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (53.8 mg, 0.131 mmol; S-Phos ligand) palladium (II) acetate (14.7 mg, 0.065 mmol) in THF (8 mL) were added K3PO4 (834 mg, 3.93 mmol) and (2,3,4-trifluorophenyl)boronic acid (276, 1.57 mmol). The reaction mixture was stirred at 70° C. under a N2 atmosphere for 16 hours, cooled to room temperature and filtered and the filtrate was concentrated by evaporation under reduced pressure. The residue was purified on a silica gel column eluting with 5 to 10% EtOAc in hexanes to provide the title intermediate (255 mg) as white solid.
Workup
- temperaturecooled to room temperature
- filtrationfiltered
- concentrationthe filtrate was concentrated by evaporation under reduced pressure
- customThe residue was purified on a silica gel column
- washeluting with 5 to 10% EtOAc in hexanes
Sources & evidence
- ORD record
- ord-103624b9257e4421b6ee88edb7a53404
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08742110B2
Reaction notes
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