Water → 4'-Hydroxy-2',6'-dimethyl-[1,1'-biphenyl]-3-carbaldehyde

HRID 507912Notes

Reaction equation

HRID 507912 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[CH:11]([C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1)=[O:12].O>C(=O)([O-])[O-].[Na+].[Na+].C(O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:11]=[O:12])[CH:18]=2)=[C:3]([CH3:10])[CH:4]=1

Participants

9

Reactant 3

HCID 962WaterHCID 819704-Bromo-3,5-dimethylphenolHCID 27343563-Formylphenylboronic acid

Product 1

HCID 231116914'-Hydroxy-2',6'-dimethyl-[1,1'-biphenyl]-3-carbaldehydeYield 83%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
80 °C

Procedure

4-Bromo-3,5-dimethylphenol (10.3 g, 51.0 mmol) and (3-formylphenyl)boronic acid (7.67 g, 51.2 mmol) were dissolved in a mixture of 1 M aqueous sodium carbonate solution (150 mL), ethanol (50 mL) and toluene (150 mL), and the air was substituted with argon gas. Tetrakis(triphenylphosphine)palladium(0) (2.95 g, 2.55 mmol) was added and the mixture was stirred under an argon atmosphere at 80° C. for 24 hr. After cooling the reaction mixture, water was added and the mixture was diluted with ethyl acetate. The insoluble material was filtered off through celite. The organic layer in the filtrate was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10%-40% ethyl acetate/hexane) to give the title compound (9.53 g, yield 83%) as pale-yellow crystals.

Workup

  1. additionwas added
  2. filtrationThe insoluble material was filtered off through celite
  3. washThe organic layer in the filtrate was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (10%-40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-04843ee5edf442f3b559932d7ecc768a
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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