Nitrobenzene → 2-Bromoanthraquinone

HRID 1719850Notes

Reaction equation

HRID 1719850 reaction equation
[N+]([C:4]1[CH:17]=[CH:16][C:15]2[C:14](=[O:18])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:19])[C:6]=2[CH:5]=1)([O-])=O.[Br:20]Br.[N+](C1C=CC=CC=1)([O-])=O>CO>[Br:20][C:4]1[CH:17]=[CH:16][C:15]2[C:14](=[O:18])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:19])[C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 7416NitrobenzeneHCID 24408BromineHCID 39285932-Nitroanthraquinone

Product 1

HCID 2210132-BromoanthraquinoneYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

1265 parts by weight of 2-nitroanthraquinone are reacted at 270° C. with elemental bromine in the presence of 60 parts by weight of nitrobenzene in a laboratory apparatus as described in Example 1. When the reaction is complete, the melt is discharged into 2,000 parts by weight of vigorously stirred methanol at 200° C. The suspension so obtained is refluxed for 1 hour, cooled to 50° C., filtered and dried, affording 1390 g of 2-bromoanthraquinone (97% yield) in 98% purity.

Workup

  1. customThe suspension so obtained
  2. temperatureis refluxed for 1 hour
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-136ca2bfdf2849dd89bad0f609631ee8
Source dataset
uspto-grants-1985_09
Patent number
US04543214

Reaction notes

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