Benzoyl Peroxide → 2-(alpha-Bromoisopropyl) anthraquinone

HRID 54867Notes

Reaction equation

HRID 54867 reaction equation
[CH:1]([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)([CH3:3])[CH3:2].[Br:20]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:20][C:1]([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)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 13725949HCID 13725949, compound

Product 1

HCID 538091792-(alpha-Bromoisopropyl) anthraquinone

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 0.95 g (3.8 mmol) 2-isopropylanthraquinone, 0.81 g (4.6 mmol) N-bromosuccinimide (NBS) and 6 mg benzoyl peroxide in 7 mL CCl4 was refluxed for 2 h under N2 with mild stirring. After cooling to room temperature, the solution was filtered through glass wool and then the CCl4 was removed under vacuum to yield a yellow liquid that solidified upon cooling. 1H-NMR showed the conversion to be complete and so the product was used without further purification.

Workup

  1. temperaturewas refluxed for 2 h under N2 with mild stirring
  2. filtrationthe solution was filtered through glass wool
  3. customthe CCl4 was removed under vacuum
  4. customto yield a yellow liquid that
  5. temperatureupon cooling
  6. customso the product was used without further purification

Sources & evidence

ORD record
ord-04dcf34c559548e8be8ef5d2f1cd8a51
Source dataset
uspto-grants-1997_04
Patent number
US05624543

Reaction notes

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