N-bromobutanimide → 5-(Bromomethyl)-3-phenyl-2,1-benzisoxazole

HRID 1198981Notes

Reaction equation

HRID 1198981 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][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:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:17][CH2:1][C:2]1[CH:3]=[CH:4][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

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 6106335-Methyl-3-phenyl-2,1-benzisoxazole

Product 1

HCID 148353455-(Bromomethyl)-3-phenyl-2,1-benzisoxazoleYield 59%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 11.7 g (0.05 g mole) of 5-methyl-3-phenyl-2,1-benzisoxazole, 10.0 g (0.056 mole) of N-bromosuccinimide and 0.1 g of dibenzoylperoxide in 200 ml of carbon tetrachloride was heated at reflux under illumination by a flood lamp for 2.5 hr. The mixture was filtered and the filtrate was washed with 5% sodium hydroxide, dried over sodium sulfate and concentrated to give a solid as residue. This solid was recrystallized twice from 2-propanol to yield 9.5 g (59%) of crystals, m.p. 130° C. (with decomposition).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under illumination by a flood lamp for 2.5 hr
  3. filtrationThe mixture was filtered
  4. washthe filtrate was washed with 5% sodium hydroxide
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto give a solid as residue
  8. customThis solid was recrystallized twice from 2-propanol

Sources & evidence

ORD record
ord-0bb75b939a414b7cbe0cec6b21387c1a
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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