Reaction #481594

ord-237bc96903554e8db12240565a2768d7

Reaction equation

CCc1ccc2c(c1)C(=O)c1ccccc1C2=O
2-ethylanthraquinone
O=C1CCC(=O)N1Br
NBS
O=C(OOC(=O)c1ccccc1)c1ccccc1
benzoyl peroxide
→
CC(Br)c1ccc2c(c1)C(=O)c1ccccc1C2=O
2-(1-bromoethyl)-anthraquinone

Reactants

CCc1ccc2c(c1)C(=O)c1ccccc1C2=O
2-ethylanthraquinone
O=C1CCC(=O)N1Br
NBS
O=C(OOC(=O)c1ccccc1)c1ccccc1
benzoyl peroxide

Reagents

None

Solvents

ClC(Cl)(Cl)Cl
CCl4

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureat reflux for 1.5 hours
  2. 2
    TemperatureOn cooling
  3. 3
    Filtrationthe precipitate is collected by filtration
  4. 4
    Washwashed on the
  5. 5
    Filtrationfilter with ethanol, hot water and finally ethanol again
  6. 6
    OtherAfter drying
  7. 7
    Otherthis may be used without further purification (i.e. recrystallisation from benzene/methanol (1:1))

Procedure

A mixture of 2-ethylanthraquinone (25 Kg, 105.9 mol), NBS (19.1 Kg, 107.3 mol) and benzoyl peroxide (70%, 200 g, 0.58 mol) in CCl4 (˜150L) is stirred at reflux for 1.5 hours. On cooling, the precipitate is collected by filtration and washed on the filter with ethanol, hot water and finally ethanol again. After drying, this may be used without further purification (i.e. recrystallisation from benzene/methanol (1:1)).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06601732B1uspto-grants-2003_08