N-bromobutanimide → 3-(4-Chlorophenyl)-7-(bromomethyl)-2,1-benzisoxazole

HRID 1198996Notes

Reaction equation

HRID 1198996 reaction equation
[Cl: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][CH:14]=[CH:13][C:12]=23)=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][N:10]=[C:11]3[C:16]([CH2:17][Br:18])=[CH:15][CH:14]=[CH:13][C:12]=23)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 156347543-(4-Chlorophenyl)-7-methyl-2,1-benzisoxazole

Product 1

HCID 156347563-(4-Chlorophenyl)-7-(bromomethyl)-2,1-benzisoxazoleYield 58%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 15.7 g (0.065 mole) of 3-(4-chlorophenyl)-7-methyl-2,1-benzisoxazole, 11.6 g (0.065 mole) of N-bromosuccinimide, 0.5 g of dibenzoylperoxide and 400 ml of carbon tetrachloride was heated at reflux while being illuminated by a flood lamp for 3 hr. The mixture was filtered and the filtrate was concentrated to give a solid as residue. The solid was recrystallized three times from acetonitrile to yield 12.0 g (58%) of crystals, m.p. 153°-155° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customwhile being illuminated by a flood lamp for 3 hr
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. customto give a solid as residue
  7. customThe solid was recrystallized three times from acetonitrile

Sources & evidence

ORD record
ord-1ce62a5860b04345ad5a0d51f6abba33
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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