Benzoyl Peroxide → HCID 19870965, compound

HRID 329571Notes

Reaction equation

HRID 329571 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([CH3:9])[CH:5]=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20].[Br:21]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(OCC)(=O)C>C(Cl)(Cl)(Cl)Cl>[Br:21][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([N:10]2[C:11](=[O:20])[C:12]3=[CH:19][CH:18]=[CH:17][CH:16]=[C:13]3[C:14]2=[O:15])=[C:2]([Cl:1])[C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 19870964HCID 19870964, compound

Product 1

HCID 19870965HCID 19870965, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 4.0 grams (0.013 mole) of N-(2,3-dichloro-4-methylphenyl)phthalimide, 2.3 grams (0.013 mole) of N-bromosuccinimide and 0.3 gram of benzoyl peroxide in 200 ml of carbon tetrachloride was heated under reflux for 22 hours. The cooled reaction mixture was poured into 500 ml of ethyl acetate. The solution was washed with three 100 ml portions of water. The organic layer was dried with magnesium sulfate and was filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished using ethyl acetate:heptane (1:4). The appropriate fractions were combined and concentrated under reduced pressure to yield 4.4 grams of N-(4-bromomethyl-2,3-dichlorophenyl)phthalimide as a solid.

Workup

  1. temperatureunder reflux for 22 hours
  2. customThe cooled reaction mixture
  3. washThe solution was washed with three 100 ml portions of water
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationwas filtered
  6. concentrationThe filtrate was concentrated under reduced pressure to a residue
  7. washElution
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c7ab51c0afd34d858acc6eadf4ec78bc
Source dataset
uspto-grants-1990_01
Patent number
US04892578

Reaction notes

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