Water → 2',6'-Dimethylbiphenyl-3-carbaldehyde

HRID 1163282Notes

Reaction equation

HRID 1163282 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1B(O)O.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>[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1[C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1

Participants

9

Reactant 3

HCID 962WaterHCID 765833-BromobenzaldehydeHCID 5833222,6-Dimethylphenylboronic acid

Product 1

HCID 230828662',6'-Dimethylbiphenyl-3-carbaldehydeYield 97%

Reagents, catalysts & solvents 5

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

Conditions

Temperature
80 °C

Procedure

3-Bromobenzaldehyde (18.5 g, 100 mmol) and (2,6-dimethylphenyl)boronic acid (21.0 g, 140 mmol) were dissolved in a mixed solvent of 1 M aqueous sodium carbonate solution (200 mL), ethanol (100 mL) and toluene (200 mL). After argon substitution, tetrakis(triphenylphosphine)palladium(0) (5.78 g, 5.00 mmol) was added. The reaction mixture was stirred under an argon atmosphere at 80° C. for 20 hr. The reaction mixture was cooled, and water was added to the reaction mixture. The mixture was diluted with ethyl acetate, and the insoluble material was filtered through celite. The organic layer of 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 (hexane-10% ethyl acetate/hexane) to give the title compound (20.4 g, yield 97%) as a colorless oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe insoluble material was filtered through celite
  3. washThe organic layer of 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 (hexane-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-07736b8a08144f1eb2b21fdbdd355f34
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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