Benzoyl Peroxide → 3,5-dibromoisobenzofuran-1(3H)-one

HRID 389936Notes

Reaction equation

HRID 389936 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[O:6][CH2:5]2.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=2)[C:7](=[O:11])[O:6]1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 6031445-Bromophthalide

Product 1

HCID 577917913,5-dibromoisobenzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a suspension of 5-bromoisobenzofuran-1(3H)-one (5 g, 23.5 mmol) in anhydrous carbon tetrachloride (50 mL) was added N-bromosuccinimide (4.18 g, 23.5 mmol) and a catalytic amount of benzoyl peroxide. The reaction mixture was heated under reflux for 2.5 hours. After cooling, the precipitated solid was filtered off, and the filtrate was concentrated on a rotary evaporator. The residual solid was partitioned between methylene chloride and water. The organic phase was washed with brine, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 20% ethyl acetate in hexanes to yield the title compound. MS (ESI) m/z 290 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2.5 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitated solid was filtered off
  5. concentrationthe filtrate was concentrated on a rotary evaporator
  6. customThe residual solid was partitioned between methylene chloride and water
  7. washThe organic phase was washed with brine
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on silica gel eluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-3d41202aa31943999f1e33e5d29532b3
Source dataset
uspto-grants-2013_02
Patent number
US08383623B2

Reaction notes

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