N-bromobutanimide → 1,2-Benzisoxazole, 6-bromo-3-(bromomethyl)-

HRID 1988871Notes

Reaction equation

HRID 1988871 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6]([CH3:9])=[N:7][O:8][C:4]=2[CH:3]=1.[Br:12]N1C(=O)CCC1=O.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6]([CH2:9][Br:12])=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 749781,1'-Azobis(cyclohexanecarbonitrile)HCID 124113226-Bromo-3-methyl-1,2-benzoxazole

Product 1

HCID 586565221,2-Benzisoxazole, 6-bromo-3-(bromomethyl)-Yield 37.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 6-bromo-3-methyl-1,2-benzisoxazole (675 mg), N-bromosuccinimide (642 mg) and 1,1′-azobis(cyclohexanecarbonitrile) (90 mg) in carbon tetrachloride (7 ml) was irradiated using a 300W lamp at reflux under nitrogen for 40 h. On cooling the precipitate was removed by filtration, the solvent was evaporated and the residue was purified by flash chromatography on a silica column (4 cm diam) eluting with a cyclohexane-ethyl acetate gradient (49:1 to 24:1) to give the title compound as a pale yellow solid (350 mg).

Workup

  1. customwas irradiated
  2. temperatureat reflux under nitrogen for 40 h
  3. temperatureOn cooling the precipitate
  4. customwas removed by filtration
  5. customthe solvent was evaporated
  6. customthe residue was purified by flash chromatography on a silica column (4 cm diam)
  7. washeluting with a cyclohexane-ethyl acetate

Sources & evidence

ORD record
ord-fc207a8ba19d4c1bb10d308b9478302c
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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