Phenylboronic Acid → 5-Phenylfuran-2-carboxylic acid

HRID 1444260Notes

Reaction equation

HRID 1444260 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7](Br)=[CH:8][CH:9]=1)=[O:4].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[C:11]1([C:7]2[O:6][C:5]([C:3]([OH:2])=[O:4])=[CH:9][CH:8]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 599633Methyl 5-bromofuran-2-carboxylate

Product 1

HCID 7362555-Phenylfuran-2-carboxylic acid

Procedure

5-Bromo-furan-2-carboxylic acid methyl ester (5) (205 mg, 1 mmol) was coupled to phenylboronic acid (146 mg, 1.2 mmol) using Method E except that once the reaction was complete, the solvents were removed in vacuo. The crude residue was re-dissolved in EtOAc (10 ml) and 1M NaOH (20 ml) was added. The aqueous layer was extracted with EtOAc (3×10 ml), and the organic layer was discarded. The aqueous layer was acidified to pH 1 with conc. HCl, and extracted with EtOAc (3×10 ml). The combined organic layers were dried (MgSO4), filtered, and the solvent removed in vacuo to give the title compound.

Workup

  1. customthe solvents were removed in vacuo
  2. dissolutionThe crude residue was re-dissolved in EtOAc (10 ml)
  3. addition1M NaOH (20 ml) was added
  4. extractionThe aqueous layer was extracted with EtOAc (3×10 ml)
  5. extractionextracted with EtOAc (3×10 ml)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d72fd24f65e3444bb06c7fd38ea172d6
Source dataset
uspto-grants-2010_02
Patent number
US07662839B2

Reaction notes

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