Benzoyl Peroxide → HCID 14519938, compound

HRID 1198623Notes

Reaction equation

HRID 1198623 reaction equation
BrN1C(=O)CCC1=O.CC1C2OC3C(=CC=CC=3C)C(=O)C=2C=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.Br[CH2:45][C:46]1[C:59]2[O:58][C:57]3[C:52](=[CH:53][CH:54]=[CH:55][C:56]=3[CH2:60][Br:61])[C:51](=[O:62])[C:50]=2[CH:49]=[CH:48][CH:47]=1>C(Cl)(Cl)(Cl)Cl>[Br:61][CH2:60][C:56]1[C:57]2[O:58][C:59]3[C:50](=[CH:49][CH:48]=[CH:47][C:46]=3[CH3:45])[C:51](=[O:62])[C:52]=2[CH:53]=[CH:54][CH:55]=1

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 14612562HCID 14612562, compoundHCID 14612563HCID 14612563, compound

Product 1

HCID 14519938HCID 14519938, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Powdered N-bromosuccinimide (5.0 g, 0.028 mol) was added to a warm solution of 4,5-dimethylxanthenone (prepared by the method of Schopff, Ber 1892, 25, 3642) in CCl4 (170 mL) containing benzoyl peroxide (40 mg), and the mixture was stirred at reflux temperature under UV irradiation (illumination) for 3 hours. Removal of the solvent under reduced pressure gave a residue which was extracted with CHCl3. The CHCl3 layer was washed with cold 1N aqueous NaOH and water (twice), then dried and evaporated to give the crude product, contaminated with starting material and the 4,5-dibromomethylxanthenone. Repeated crystallization from benzene-petroleum ether gave pure material as colourless needles (1.96 g, 29%), m.p. 171°-172° C. Anal. (C15H11BrO2) C,H,Br.

Workup

  1. temperatureat reflux temperature
  2. customunder UV irradiation (illumination) for 3 hours
  3. customRemoval of the solvent under reduced pressure
  4. customgave a residue which
  5. extractionwas extracted with CHCl3
  6. washThe CHCl3 layer was washed with cold 1N aqueous NaOH and water (twice),
  7. customthen dried
  8. customevaporated
  9. customto give the crude product
  10. customcrystallization from benzene-petroleum ether

Sources & evidence

ORD record
ord-2865cc1b151e4ff4b00b4caaa36f15c6
Source dataset
uspto-grants-1994_01
Patent number
US05281620

Reaction notes

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