Ethanol → 4-(Pyridin-3-yl)benzaldehyde

HRID 1784661Notes

Reaction equation

HRID 1784661 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](OB(O)O)=[CH:5][CH:4]=1)=[O:2].C(=O)([O-])[O-].[Na+].[Na+].C(O)C.Br[C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1>C1(C)C=CC=CC=1.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.O>[N:25]1[CH:26]=[CH:27][CH:28]=[C:23]([C:6]2[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=2)[CH:24]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 122863-BromopyridineHCID 21940015p-Formylphenylboric acid

Product 1

HCID 36930464-(Pyridin-3-yl)benzaldehydeYield 25.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (0.65 g, 0.56 mmol), 4-formylphenylboric acid (2.81 g, 18.7 mmol), 2M aqueous sodium carbonate (18.7 ml, 37.4 mmol) and ethanol were added to the nitrogen-saturated solution of 3-bromopyridine (2.66 g, 16.8 mmol) in toluene and refluxed under nitrogen for 8 hrs. Water was added to the solution and extracted with ethyl acetate, washed with water and brine and dried. Solvents were removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=1/1.5) to give 4-(3-pyridyl)benzaldehyde (0.78 g, 25%).

Workup

  1. temperaturerefluxed under nitrogen for 8 hrs
  2. extractionextracted with ethyl acetate
  3. washwashed with water and brine
  4. customdried
  5. customSolvents were removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=1/1.5)

Sources & evidence

ORD record
ord-f69f463b37f64448b84e3814c8772d08
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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