Benzoyl Peroxide → HCID 14835374, compound

HRID 1199003Notes

Reaction equation

HRID 1199003 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:17])[C:5]2[C:6]([CH:16]=1)=[C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[O:8][N:9]=2.[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:17][C:4]1[C:5]2[C:6](=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:8][N:9]=2)[CH:16]=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 14835373HCID 14835373, compound

Product 1

HCID 14835374HCID 14835374, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 16.2 g (0.067 mole) of 5-chloro-7-methyl-3-phenyl-2,1-benzisoxazole, 11.9 g (0.067 mole) of N-bromosuccinimide, 275 ml of carbon tetrachloride and 0.1 g of dibenzoylperoxide was heated at reflux under illumination of a flood lamp for 2 hr. The mixture was filtered and the filtrate was washed once with a saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated to give a yellow solid as residue. An NMR analysis of the residue showed it was a mixture containing 8% of starting methyl compound, 83% of monobromo compound and 9% of dibromo compound. An analytical sample, m.p. 142°-144° C., was obtained by recrystallizing twice from ethyl acetate.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under illumination of a flood lamp for 2 hr
  3. filtrationThe mixture was filtered
  4. washthe filtrate was washed once with a saturated sodium bicarbonate solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto give a yellow solid as residue
  8. customAn analytical sample, m.p. 142°-144° C., was obtained
  9. customby recrystallizing twice from ethyl acetate

Sources & evidence

ORD record
ord-05354f63b49849e1bdd80aaa8fe2ca78
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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