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Sodium Carbonate → 4-(3-Chloropyridin-2-yl)benzaldehyde

HRID 578595
Notes
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Reaction equation

HRID 578595 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:9]([C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1)=[O:10].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O.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>[Cl:8][C:7]1[C:2]([C:14]2[CH:15]=[CH:16][C:11]([CH:9]=[O:10])=[CH:12][CH:13]=2)=[N:3][CH:4]=[CH:5][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 169882,3-DichloropyridineHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 534262384-(3-Chloropyridin-2-yl)benzaldehydeYield 83%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst
HCID 702
Ethanol
Solvent
HCID 962WaterSolvent

Procedure

{circle around (2)} 100 g (0.676 mol) of 2,3-dichloropyridine was dissolved in 500 mL of ethanol, and 101.4 g (0.676 mol) of (4-formylphenyl)boronic acid and 78 g (0.0676 mol) of Pd(PPh3)4 were sequentially added. A solution of 86 g (0.811 mol) of sodium carbonate in 500 mL of distilled water was placed in the reactor, and the mixture was heated to reflux for 4˜6 hours so as to allow it to react. After completion of the reaction, the reaction solution was concentrated under reduced pressure to remove ethanol, and extracted with ethyl acetate. The extract was treated with magnesium sulfate, filtered and concentrated under reduced pressure, yielding 4-(3-chloropyridin-2-yl)benzaldehyde as represented below in a 83% yield.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4˜6 hours so as
  3. customto react
  4. customAfter completion of the reaction
  5. concentrationthe reaction solution was concentrated under reduced pressure
  6. customto remove ethanol
  7. extractionextracted with ethyl acetate
  8. additionThe extract was treated with magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-457b93768f514804b71f452fc742b93d
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09040572B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes