Benzoyl Peroxide → HCID 86619723, compound

HRID 221951Notes

Reaction equation

HRID 221951 reaction equation
[C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([N:7]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:17])=[CH:3][CH:2]=1.[Br:19]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:18][C:1]1[CH:2]=[CH:3][C:4]([N:7]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:17])=[CH:5][CH:6]=1.[Br-:19]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 6169991H-Isoindole-1,3(2H)-dione, 2-(4-methylphenyl)-

Product 1

HCID 86619723HCID 86619723, compoundYield 121.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture of 2-p-tolylisoindol-1,3-dione (A) (4.0 g, 17 mmol) and N-bromosuccinimide (3.0 g, 17 mmol) there were added carbon tetrachloride (70 mL) and benzoyl peroxide (8 mL) and the mixture was heated to the boil under halogen radiation over a period of 2 h. The resulting reaction solution was concentrated. The residue was stirred with chloroform (300 mL) with heating for 15 min and the mixture then filtered hot for isolation of the resulting solid matter. The filtrate was concentrated in vacuo, and the residue was purified by column chromatography (SiO2 (150 g) using cyclohexane/EtOAc 4:1 (2000 mL) as eluent). The bromide 2-(4-bromomethylphenyl)isoindol-1,3-dione (B) (4.1 g, 77%) was isolated as a white solid having a melting point of 191-199° C.

Workup

  1. temperaturethe mixture was heated to the boil under halogen radiation over a period of 2 h
  2. customThe resulting reaction solution
  3. concentrationwas concentrated
  4. temperaturewith heating for 15 min
  5. filtrationthe mixture then filtered hot for isolation of the resulting solid matter
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by column chromatography (SiO2 (150 g) using cyclohexane/EtOAc 4:1 (2000 mL) as eluent)

Sources & evidence

ORD record
ord-f563c47c14dd4f27826e75f349678df8
Source dataset
uspto-grants-2012_06
Patent number
US08207182B2

Reaction notes

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