Benzoyl Peroxide → 3-Bromo-5,6-dichloro-3H-isobenzofuran-1-one

HRID 1091442Notes

Reaction equation

HRID 1091442 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[C:7](=[O:12])[O:6][CH2:5]2.[Br:13]NC(=O)CCC(N)=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)Cl>[Br:13][CH:5]1[C:4]2[C:8](=[CH:9][C:10]([Cl:11])=[C:2]([Cl:1])[CH:3]=2)[C:7](=[O:12])[O:6]1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 9834204N-BromosuccinamideHCID 144180775,6-Dichloro-3H-isobenzofuran-1-one

Product 1

HCID 144180783-Bromo-5,6-dichloro-3H-isobenzofuran-1-oneYield 99.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of 5,6-Dichloro-3H-isobenzofuran-1-one (1.45 g), N-bromosuccinamide (1.27 g) and catalytic benzoyl peroxide in chloroform (30 mL) was heated to reflux for 1 hour. After cooling, the reaction mixture was washed with water, brine, dried (magnesium sulfate), filtered and concentrated to give the sub-title compound as a white solid (1.82 g, 91%). 1H NMR (400 MHz, CDCl3) δ 7.36 (1H, s), 7.77 (1H, s), 8.03 (1H, s) ppm.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with water, brine
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d3763462961f40439aea8db9137528f3
Source dataset
uspto-grants-2012_03
Patent number
US08129381B2

Reaction notes

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