1-Bromo-2-methylnaphthalene → 3-(2-Methylnaphthalen-1-yl)benzaldehyde

HRID 2422256Notes

Reaction equation

HRID 2422256 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH3:12].[CH:13]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)=[O:14]>C(=O)([O-])[O-].[Na+].[Na+].C(O)C.C1(C)C=CC=CC=1.O.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>[CH3:12][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]=1[C:19]1[CH:20]=[C:15]([CH:16]=[CH:17][CH:18]=1)[CH:13]=[O:14]

Participants

9

Reactant 2

HCID 757541-Bromo-2-methylnaphthaleneHCID 27343563-Formylphenylboronic acid

Product 1

HCID 230830313-(2-Methylnaphthalen-1-yl)benzaldehydeYield 65%

Reagents, catalysts & solvents 6

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
80 °C

Procedure

1-Bromo-2-methylnaphthalene (3.32 g, 15.0 mmol) and (3-formylphenyl)boronic acid (2.13 g, 15.0 mmol) was dissolved in a mixture of 1 M sodium carbonate aqueous solution (30 mL), ethanol (15 mL) and toluene (30 mL) and, after argon substitution, tetrakis(triphenylphosphine)palladium (0) (0.867 g, 0.750 mmol) was added. The reaction mixture was stirred under an argon atmosphere at 80° C. for 24 hrs. The reaction mixture was cooled, diluted with water and 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-20% ethyl acetate/hexane) to give the title compound (2.39 g, yield 65%) as a pale-yellow 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-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-052080beb3114ebfaa9997b2d51d07d0
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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