Hydrochloric Acid → 4,5-Dibromofuran-2-carboxylic acid

HRID 2265192Notes

Reaction equation

HRID 2265192 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10]C)=[O:9])[O:5][C:6]=1[Br:7].[Li+].[OH-].Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([OH:10])=[O:9])[O:5][C:6]=1[Br:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 4135083Methyl 4,5-Dibromo-2-furancarboxylate

Product 1

HCID 41948324,5-Dibromofuran-2-carboxylic acidYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methyl 4,5-dibromo-2-furoate (26.19 g, 92.2 mmol) in THF (60 mL) at rt was added LiOH (3 M in water, 60 mL, 180 mmol). The biphasic mixture was stirred for 4 h. The mixture was poured into 1 N HCl (500 mL) and extracted with DCM (3×). The combined organic layers were dried (Na2SO4) and concentrated to provide 24.59 g (99%) of the acid as an off-white solid. 1H NMR (400 MHz, CD3OD): 7.30 (s, 1H).

Workup

  1. extractionextracted with DCM (3×)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-373a91dd3ec846a09b1f3033a6c41751
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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