Potassium Carbonate → 4-Chloro-3-(4-methoxyphenyl)benzenecarboxaldehyde

HRID 2113105Notes

Reaction equation

HRID 2113105 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH:16]=[O:17].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(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>[Cl:21][C:20]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][C:13]=1[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 140498093-Bromo-4-chlorobenzaldehyde

Product 1

HCID 223913894-Chloro-3-(4-methoxyphenyl)benzenecarboxaldehydeYield 62.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Procedure

To a degassed solution of 4-methoxybenzeneboronic acid (1.51 g, 10 mmol), 3-bromo-4-chlorobenzaldehyde (2 g, 9.13 mmol), and potassium carbonate (3.13 g, 22.8 mmol) in toluene/ethanol 2/1, (60 mL), Pd(PPh3)4 (130 mg, 1 mol %) is added and the mixture is degassed for further 5 minutes. The mixture is then refluxed for 2 days. The mixture was partitioned between ethyl acetate and water and extracted. The organic solvent was dried over sodium sulphate, removed under reduced pressure, and the residue purified by column chromatography (heptane/ethyl acetate 19/1 to afford 1.41 g of product.

Workup

  1. customthe mixture is degassed for further 5 minutes
  2. temperatureThe mixture is then refluxed for 2 days
  3. customThe mixture was partitioned between ethyl acetate and water
  4. extractionextracted
  5. dry with materialThe organic solvent was dried over sodium sulphate
  6. customremoved under reduced pressure
  7. customthe residue purified by column chromatography (heptane/ethyl acetate 19/1

Sources & evidence

ORD record
ord-17cca8dde8d747c1a83076c6fd8688f5
Source dataset
uspto-grants-2009_04
Patent number
US07524873B2

Reaction notes

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