Potassium Phosphate, Tribasic → 5-Phenylfuran-2-carboxylic acid

HRID 1171487Notes

Reaction equation

HRID 1171487 reaction equation
Br[C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=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[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 685115-Bromo-2-furanecarboxylic acid

Product 1

HCID 7362555-Phenylfuran-2-carboxylic acidYield 55.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 5-bromofuran-2-carboxylic acid (381 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 209 mg of 5-phenylfuran-2-carboxylic acid. MS (ES−) found: (M−H)−=187.13.

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-401cf477621d49ad9a5bb97c3c306062
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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