Sodium Carbonate → HCID 89461069, compound

HRID 926437Notes

Reaction equation

HRID 926437 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[CH:12]3[CH:16]([OH:19])[CH:17]([OH:18])[CH:5]([C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:4]=2[CH:3]=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([CH:17]=[O:18])[C:6]3[C:11]([C:12]=2[CH:16]=[O:19])=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 89461092HCID 89461092, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 89461069HCID 89461069, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Diol intermediate 12a (1.58 g, 5.0 mmol, 1 equiv.) was dissolved in anhydrous acetonitrile (100 mL) and heated to reflux with stirring and formed a transparent, light-tan solution. Lead tetraacetate (4.42 g, 10.0 mmol, 2 equiv.) was added portion-wise to the solution over a period of 5 minutes, quickly turning the solution opaque and brown in color. The solution was then stirred at reflux for 4 hours, resulting in the formation of a dark-orange precipitate within the brown solution. The consumption of the diol intermediates were monitored through thin-layer chromatography (80% CH2Cl2/ethyl acetate, Rf=0.50 & Rf=0.33). After the reaction was complete, the reaction mixture was concentrated via rotary evaporation and gave a burgundy residue. 10% aqueous sodium carbonate (300 mL) was added to the residue, allowing the residue to be suspended in the aqueous solution. The organic contents were extracted from the aqueous layer using dichloromethane. The opaque, yellow organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to give a yellow-orange solid residue. The residue was purified by column chromatography (20% ethyl acetate/hexane, Rf=0.29), providing 2-bromo-9,10-anthracenedialdehyde 13 as an orange solid (1.23 g, 80%). 1H NMR (CDCl3): δ 11.43 (s, 1H), 11.42 (s, 1H), 9.03 (s, 1H), 8.72 (m, 2H), 8.66 (d, 1H), 7.75 (m, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customformed a transparent, light-tan solution
  4. stirringThe solution was then stirred
  5. temperatureat reflux for 4 hours
  6. customresulting in the formation of a dark-orange precipitate within the brown solution
  7. customThe consumption of the diol intermediates
  8. concentrationthe reaction mixture was concentrated via rotary evaporation
  9. customgave a burgundy residue
  10. extractionThe organic contents were extracted from the aqueous layer
  11. dry with materialThe opaque, yellow organic layer was dried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customto give a yellow-orange solid residue
  15. customThe residue was purified by column chromatography (20% ethyl acetate/hexane, Rf=0.29)

Sources & evidence

ORD record
ord-0a15ef2714ca41bebdb1feae8b1c3ffa
Source dataset
uspto-grants-2016_03
Patent number
US09285320B2

Reaction notes

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