Potassium Carbonate → 6-(Cyclopropylmethoxy)-4′-methoxy[1,1′-biphenyl]-3-carboxaldehyde

HRID 2113117Notes

Reaction equation

HRID 2113117 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH:12]1[CH2:14][CH2:13]1)[CH:5]=[O:6].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.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>[CH:12]1([CH2:11][O:10][C:9]2[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=2[C:20]2[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 22391279HCID 22391279, compound

Product 1

HCID 223915076-(Cyclopropylmethoxy)-4′-methoxy[1,1′-biphenyl]-3-carboxaldehydeYield 89.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Procedure

To a degassed solution of 3-bromo-4-cyclopropylmethoxybenzaldehyde (1.53 g, 6 mmol), 4-methoxybenzeneboronic acid (1.22 g, 8 mmol) and potassium carbonate (2.74 g, 20 mmol) in toluene/ethanol 2/1 (40 mL), Pd(PPh3)4 (100 mg) was added and the mixture was degassed for further 5 minutes. The mixture was then refluxed for 12 hours. The solid is filtered off, and the solvent partitioned between ethyl acetate and water and extracted. The organic solvent was removed under reduced pressure, dried over sodium sulphate and purified by column chromatography on silica (hexane/ethyl acetate 8/2) to afford 1.52 g of product.

Workup

  1. customthe mixture was degassed for further 5 minutes
  2. temperatureThe mixture was then refluxed for 12 hours
  3. filtrationThe solid is filtered off
  4. customthe solvent partitioned between ethyl acetate and water
  5. extractionextracted
  6. customThe organic solvent was removed under reduced pressure
  7. dry with materialdried over sodium sulphate
  8. custompurified by column chromatography on silica (hexane/ethyl acetate 8/2)

Sources & evidence

ORD record
ord-78aba6adfc49485798c6201c9feafca7
Source dataset
uspto-grants-2009_04
Patent number
US07524873B2

Reaction notes

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