Benzoyl Peroxide → HCID 14835382, compound

HRID 1199007Notes

Reaction equation

HRID 1199007 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][N:10]=[C:11]3[C:16]([CH3:17])=[CH:15][C:14]([Cl:18])=[CH:13][C:12]=23)=[CH:4][CH:3]=1.[Br:19]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:17][C:16]1[C:11]2[C:12](=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=3)[O:9][N:10]=2)[CH:13]=[C:14]([Cl:18])[CH:15]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 14835381HCID 14835381, compound

Product 1

HCID 14835382HCID 14835382, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2.1 g (0.0065 mole) of 3-(4-bromophenyl)-5-chloro-7-methyl-2,1-benzisoxazole, 1.2 g (0.0067 mole) of N-bromosuccinimide and a few crystals of dibenzoyl peroxide in 100 ml of carbon tetrachloride was heated at reflux for 2.5 hr under flood light illumination and an argon atmosphere and then filtered while still hot. The filtrate was concentrated under reduced pressure to a solid residue. The solid was recrystallized twice from 2-propanol to give 2.2 g (85%) of light-yellow needles, m.p. 147°-150° C.

Workup

  1. temperatureat reflux for 2.5 hr under flood light illumination
  2. filtrationan argon atmosphere and then filtered while still hot
  3. concentrationThe filtrate was concentrated under reduced pressure to a solid residue
  4. customThe solid was recrystallized twice from 2-propanol

Sources & evidence

ORD record
ord-fd6b6b38797043f3a8e36177e19a8d25
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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