3-Furoic acid → 5-Bromofuran-3-carboxylic acid

HRID 1921808Notes

Reaction equation

HRID 1921808 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=[O:7])=[CH:2]1.[BrH:9].[NH+]1C=CC=CC=1>C(O)(=O)C>[Br:9][C:5]1[O:1][CH:2]=[C:3]([C:6]([OH:8])=[O:7])[CH:4]=1

Participants

4

Reactant 2

HCID 102683-Furoic acidHCID 21226041Pyridinium hydrobromide

Product 1

HCID 133335605-Bromofuran-3-carboxylic acidYield 21%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

Furan-3-carboxylic acid (1 g, 8.93 mmol) is added to a solution of pyridinium hydrobromide perbromide (3.02 g, 9.46 mmol) in acetic acid (5 mL). The reaction mixture is stirred at 50° C. for 5 hours, then at room temperature overnight. After removing the solvent in vacuo, water is added and a precipitate is formed. The solid is collected by filtration and dried to yield the title compound (0.364 g, 21%). HPLC (254 nm): Rt 2.65 min (88%).

Workup

  1. customat room temperature
  2. customovernight
  3. customAfter removing the solvent in vacuo, water
  4. additionis added
  5. customa precipitate is formed
  6. filtrationThe solid is collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-25379fce5adc4afe817894eea035817d
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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