Potassium Phosphate, Tribasic → 4-Phenylfuran-2-carboxylic acid

HRID 1171486Notes

Reaction equation

HRID 1171486 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:7]([OH:9])=[O:8])[O:5][CH:6]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C>[C:10]1([C:2]2[CH:3]=[C:4]([C:7]([OH:9])=[O:8])[O:5][CH:6]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 122394464-Bromofuran-2-carboxylic acid

Product 1

HCID 131539344-Phenylfuran-2-carboxylic acidYield 50.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 4-bromofuran-2-carboxylic acid (380 mg, 2 mmol), phenylboronic acid (488 mg, 4 mmol) in DMF (3 ml) was place in a microwave reaction tube and treated with a 2 M K3PO4(aq) (2 ml, 4 mmol). The solution was purged with nitrogen for 10 minutes before adding Pd(PPh3)4 (1.5 mg) catalyst. The mixture was again purged with nitrogen for 5 minutes before the reaction tube was sealed. The mixture was heated in a microwave oven at 150° C. for 30 minutes. The reaction mixture was filtered and the filtrate poured into 1N HCl (100 ml) with stirring. The precipitate was filtered and air-dried to give 190 mg of 4-phenylfuran-2-carboxylic acid. MS (ES−) found: (M−H)−=187.07.

Workup

  1. customin a microwave reaction tube
  2. customThe solution was purged with nitrogen for 10 minutes
  3. additionbefore adding Pd(PPh3)4 (1.5 mg) catalyst
  4. customThe mixture was again purged with nitrogen for 5 minutes before the reaction tube
  5. customwas sealed
  6. filtrationThe reaction mixture was filtered
  7. additionthe filtrate poured into 1N HCl (100 ml)
  8. filtrationThe precipitate was filtered
  9. customair-dried

Sources & evidence

ORD record
ord-10dce3c1d5264790853df5533e8b1280
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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