Potassium Carbonate → Ethyl (5-bromobenzofuran)-2-carboxylate

HRID 413685

Reaction equation

HRID 413685 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[CH:4][CH:3]=1.Br[CH:12](C(OCC)=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][C:6]=2[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69637Diethyl bromomalonateHCID 728635-Bromosalicylaldehyde

Product 1

HCID 735184Ethyl (5-bromobenzofuran)-2-carboxylateYield 26.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-bromosalicylaldehyde (10 g, 50 mmol), diethyl bromomalonate (13.1 g, 55 mmol), potassium carbonate (6.9 g, 50 mmol), and 2-butanone (80 mL) was stirred at 90° C. for 16 hrs. The solvent was removed under reduced pressure at 45° C., and the residue was acidified with 1M HCl, extracted, washed, dried, and evaporated. The residue was purified by chromatography to give about 3.6 g of ethyl 5-bromo-benzofuran-2-carboxylate, mp. 59-60° C.

Workup

  1. customThe solvent was removed under reduced pressure at 45° C.
  2. extractionextracted
  3. washwashed
  4. customdried
  5. customevaporated
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-372b236d8c5e479eaf39398b6b9dbca7
Source dataset
uspto-grants-2003_05
Patent number
US06569860B2

Linked notes

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