Bromine → HCID 19696159, compound

HRID 863516Notes

Reaction equation

HRID 863516 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH:10]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2].C([O-])(=O)C.[Na+].[Br:24]Br>C(O)(=O)C>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[Br:24])[CH:10]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 19696175HCID 19696175, compound

Product 1

HCID 19696159HCID 19696159, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5-acetamido-2-carboxyethylindane (18 g, 73 mmol), sodium acetate (9 g, 110 mmol) in acetic acid (300 mL) was treated dropwise with bromine (14.1 g, 88 mmol) and then stirred for 18 h. After removing the solvent, the residue was dissolved in an ether:water mixture, and sodium bisulfite was added. The ether layer was separated and the aqueous layer back extracted. The combined organic layers were washed with saturated NaCl, dried over magnesium sulfate, filtered and evaporated. The syrup was purified by silica gel chromatography (3:2 hexane:EtOAc) to give the product.

Workup

  1. customAfter removing the solvent
  2. dissolutionthe residue was dissolved in an ether
  3. additionwater mixture, and sodium bisulfite was added
  4. customThe ether layer was separated
  5. extractionthe aqueous layer back extracted
  6. washThe combined organic layers were washed with saturated NaCl
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe syrup was purified by silica gel chromatography (3:2 hexane:EtOAc)
  11. customto give the product

Sources & evidence

ORD record
ord-e1e4bc576ab4423eb933e907f902d8e0
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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