Sodium Carbonate → 4'-Chloro-2,6-dimethyl-[1,1'-biphenyl]-4-carbaldehyde

HRID 1520275Notes

Reaction equation

HRID 1520275 reaction equation
FC(F)(F)S(O[C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH:14]=[O:15])=[CH:9][C:8]=1[CH3:16])(=O)=O.[Cl:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C1(C)C=CC=CC=1>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:7]2[C:12]([CH3:13])=[CH:11][C:10]([CH:14]=[O:15])=[CH:9][C:8]=2[CH3:16])=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 544771104-Formyl-2,6-dimethylphenyl trifluoromethanesulfonate

Product 1

HCID 1178404464'-Chloro-2,6-dimethyl-[1,1'-biphenyl]-4-carbaldehyde

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A reaction mixture of 4-formyl-2,6-dimethylphenyl trifluoromethanesulfonate (2.17 g), 4-chlorophenylboronic acid (1.80 g), tris(dibenzylideneacetone)dipalladium (0.282 g), 2,6-dimethoxy-2′-(dicyclohexylphosphino)biphenyl (0.505 g), sodium carbonate (2.45 g), toluene (34.5 mL) and water (11.5 mL) was stirred at 100° C. overnight under a nitrogen atmosphere. The insoluble material was filtered off through celite, and the filtrate was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound.

Workup

  1. filtrationThe insoluble material was filtered off through celite
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8d4e59f9d7c443f299c397ecebd040ea
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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