HCID 22144870, compound → HCID 22144851, compound

HRID 1824923Notes

Reaction equation

HRID 1824923 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([Br:16])[C:7]2[O:11][C:10]([C:12]([O-:14])=[O:13])=[CH:9][C:8]=2[CH:15]=1)([O-:3])=[O:2].[K+]>CO>[N+:1]([C:4]1[CH:5]=[C:6]([Br:16])[C:7]2[O:11][C:10]([C:12]([OH:14])=[O:13])=[CH:9][C:8]=2[CH:15]=1)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 22144870HCID 22144870, compound

Product 1

HCID 22144851HCID 22144851, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 11.5 gm (35.5 mMol) potassium 5-nitro-7-bromobenzofuran-2-carboxylate and 36 gm Dowex 50WX8-200 resin in 1.6 L methanol was stirred for 1 hour at room temperature. The mixture was filtered and the filtrate concentrated under reduced pressure. The residue was diluted with about 80 mL of methanol and heated on the steam bath with stirring. The mixture was cooled to room temperature and filtered. The residual solid was dried under vacuum to provide 6.7 gm (66%) of the desired compound as a gold solid.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. additionThe residue was diluted with about 80 mL of methanol
  4. temperatureheated on the steam bath
  5. stirringwith stirring
  6. temperatureThe mixture was cooled to room temperature
  7. filtrationfiltered
  8. customThe residual solid was dried under vacuum

Sources & evidence

ORD record
ord-2d12051314c644bfb4ba991a460b58ac
Source dataset
uspto-grants-2006_05
Patent number
US07045545B1

Reaction notes

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