Ethanol → Ethyl (5-bromobenzofuran)-2-carboxylate

HRID 1603889Notes

Reaction equation

HRID 1603889 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([OH:12])=[O:11])=[CH:7][C:6]=2[CH:13]=1.S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([O:12][CH2:19][CH3:20])=[O:11])=[CH:7][C:6]=2[CH:13]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 7352475-Bromo-2-benzofurancarboxylic acid

Product 1

HCID 735184Ethyl (5-bromobenzofuran)-2-carboxylateYield 93%

Procedure

A solution of 5-bromo-2-benzofurancarboxylic acid (5.01 g, 20.8 mmol) in absolute ethanol (150 ml) was added with concentrated sulfuric acid (15 ml) and the mixture was refluxed under stirring for 2 h. After this time, the volatiles were evaporated off under reduced pressure and the resulting residue was neutralized with a sodium bicarbonate saturated solution and extracted with ethyl ether (4×100 ml). The mixture was dried and the solvent was evaporated off under reduced pressure, to obtain 5.19 g of the title compound as a white solid with melting point 58-60° C. (93% yield).

Workup

  1. temperaturethe mixture was refluxed
  2. customAfter this time, the volatiles were evaporated off under reduced pressure
  3. extractionextracted with ethyl ether (4×100 ml)
  4. customThe mixture was dried
  5. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-bb9ab76924f3425d8d8322bc3fee41ba
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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