Acetic Acid → HCID 21245416, compound

HRID 620905Notes

Reaction equation

HRID 620905 reaction equation
[Cl:1][C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2OC)[C:9]([OH:18])=[C:8]2[C:3]=1[C:4](=[O:20])[CH:5]=[CH:6][C:7]2=[O:19].[Br:21]Br.[C:23]([OH:26])(=O)C>>[Br:21][C:6]1[C:7](=[O:19])[C:8]2[C:3]([C:4](=[O:20])[CH:5]=1)=[C:2]([Cl:1])[C:15]1[C:10](=[C:11]([O:26][CH3:23])[CH:12]=[CH:13][CH:14]=1)[C:9]=2[OH:18]

Participants

4

Reactant 3

HCID 176Acetic Acid2×HCID 24408BromineHCID 21245419HCID 21245419, compound2×

Product 1

HCID 21245416HCID 21245416, compound

Procedure

10-Chloro-9-hydroxy-5-methoxy-1,4-anthracenedione (compound 12) (50 mg) was dissolved in acetic acid (5 ml) to saturation by warming. The mixture was cooled to room temperature before addition of bromine (27 mg) in acetic acid (0.15 ml). The mixture was stirred for 120 min. then excess acetic acid was evaporated under reduced pressure. The crude solid dibromide was dissolved in ethanol (5 ml) containing boron trifluoride etherate (5 drops) and heated at reflux for 20 min. The resulting red-purple solution which deposited some crystals was cooled and diluted with distilled water (20 ml). After standing overnight, the precipitated red-black solid was filtered off to give the product (compound 13) (58 mg, 91%).

Workup

  1. temperatureby warming
  2. customexcess acetic acid was evaporated under reduced pressure
  3. dissolutionThe crude solid dibromide was dissolved in ethanol (5 ml)
  4. additioncontaining boron trifluoride etherate (5 drops)
  5. temperatureheated
  6. temperatureat reflux for 20 min
  7. temperaturewas cooled
  8. additiondiluted with distilled water (20 ml)
  9. waitAfter standing overnight
  10. filtrationthe precipitated red-black solid was filtered off

Sources & evidence

ORD record
ord-53bf926f098d462fa5ccc9bcfd6c43ca
Source dataset
uspto-grants-1989_04
Patent number
US04822873

Reaction notes

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