Ethanol → Ethyl 5-bromofuran-2-carboxylate

HRID 1654126Notes

Reaction equation

HRID 1654126 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH2:14](O)[CH3:15]>>[Br:1][C:2]1[O:6][C:5]([C:7]([O:9][CH2:14][CH3:15])=[O:8])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 685115-Bromo-2-furanecarboxylic acid

Product 1

HCID 345282Ethyl 5-bromofuran-2-carboxylate

Procedure

10 g of 5-bromo-2-furancarboxylic acid were refluxed for 24 hours in 200 ml of ethanol in the presence of 2 ml of thionyl chloride. The solvent was evaporated and the residue was poured into an aqueous sodium bicarbonate solution. The mixture was extracted with ethyl acetate and the extract was dried. The solvent was evaporated to obtain 8.5 g of the expected product.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was poured into an aqueous sodium bicarbonate solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. customthe extract was dried
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a09c3e24a9ce46c3ae9af49082cd4a61
Source dataset
uspto-grants-1995_04
Patent number
US05405865

Reaction notes

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