Phenylboronic Acid → 3-Phenyl-2-furoic acid

HRID 472675

Reaction equation

HRID 472675 reaction equation
Br[C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([OH:9])=[O:8].[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])(O)=O.[Na+]>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>[C:10]1([C:2]2[CH:6]=[CH:5][O:4][C:3]=2[C:7]([OH:9])=[O:8])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 6054793-Bromofuran-2-carboxylic acid

Product 1

HCID 88997083-Phenyl-2-furoic acidYield 70%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

To 3-bromo-2-furancarboxylic acid (540 mg, 2.8 mmol dissolved in DME (105 ml)) was added of (Ph3P)4Pd (936 mg, 0.81 mmol), and the resulting solution was stirred at room temperature for 15 min. The mixture was treated with 500 mg (3.0 mmol) of benzene boronic acid, an aqueous solution of 2M NaHCO3 (4 mmol) and heated to reflux for 10 hours. After cooling to room temperature, the solvent was partially removed under reduced pressure, and the resulting mixture was extracted twice with diethyl ether. The water layer was acidified with 10% HCl and extracted with ethyl acetate (5 times). The combined organic layers were washed with brine, dried (Na2SO4), and evaporated under reduced pressure. The residue was crystallized from a mixture of n-hexane/ethyl acetate (about 8:2) to give the title compound. Yield: 70%.

Workup

  1. temperatureto reflux for 10 hours
  2. temperatureAfter cooling to room temperature
  3. customthe solvent was partially removed under reduced pressure
  4. extractionthe resulting mixture was extracted twice with diethyl ether
  5. extractionextracted with ethyl acetate (5 times)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated under reduced pressure
  9. customThe residue was crystallized from a mixture of n-hexane/ethyl acetate (about 8:2)

Sources & evidence

ORD record
ord-767f477d260449c38f28649c1fde450a
Source dataset
uspto-grants-2014_01
Patent number
US08633215B2

Linked notes

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