Sodium Hydroxide → 7-bromobenzofuran-5-carboxylic acid

HRID 1824933Notes

Reaction equation

HRID 1824933 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([Br:14])[C:8]2[O:12][CH:11]=[CH:10][C:9]=2[CH:13]=1)=[O:4].[OH-].[Na+]>C(O)C>[C:3]([C:5]1[CH:6]=[C:7]([Br:14])[C:8]2[O:12][CH:11]=[CH:10][C:9]=2[CH:13]=1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22144801HCID 22144801, compound

Product 1

HCID 221447517-bromobenzofuran-5-carboxylic acidYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.52 gm (2.03 mMol) 5-methoxycarbonyl-7-bromobenzofuran and 0.41 gm (10.13 mMol) sodium hydroxide in 4 mL ethanol was stirred at room temperature until all of the starting material had been consumed. The reaction mixture was concentrated under reduced pressure and the residue dissolved in water. This solution was then made basic by the addition of 1N sodium hydroxide and was extracted well with ethyl acetate. The remaining aqueous phase was made acidic (pH about 2) by treatment with potassium hydrogen sulfate and the resulting solid removed by filtration. The aqueous phase was extracted well with ethyl acetate and the organics were combined and concentrated under reduced pressure to provide 0.40 gm (82%) of 5-carboxy-7-bromobenzofuran as an off-white solid.

Workup

  1. customhad been consumed
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue dissolved in water
  4. additionThis solution was then made basic by the addition of 1N sodium hydroxide
  5. extractionwas extracted well with ethyl acetate
  6. customthe resulting solid removed by filtration
  7. extractionThe aqueous phase was extracted well with ethyl acetate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-74752336941b4abc851d336b053172d9
Source dataset
uspto-grants-2006_05
Patent number
US07045545B1

Reaction notes

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