Benzoyl Peroxide → HCID 13109084, compound

HRID 543499Notes

Reaction equation

HRID 543499 reaction equation
[F:1][CH2:2][CH:3]([N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18])[CH2:4][C:5]([CH3:7])=[CH2:6].[Br:19]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[F:1][CH2:2][CH:3]([N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18])[CH2:4][C:5](=[CH2:7])[CH2:6][Br:19]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 13109083HCID 13109083, compound

Product 1

HCID 13109084HCID 13109084, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1-fluoro-2-phthalimido-4-methyl-4-pentene (28.3 g, 115 mmoles) prepared as in step B above, N-bromosuccinimide (20.4 g, 115 mmoles), carbontetrachloride (300 mL), and a few mgs of benzoyl peroxide is heated under strong reflux (325 W lamp) during 7.5 hours. After cooling and filtration, the solution is washed with water (100 mL, 3 times), dried over magnesium sulfate and concentrated. The oily residue (quantitative), consisting mainly of the title compound plus some 1-fluoro-2-phthalimido-4-methyl-5-bromo-3-pentene, is used for the next step without further purification.

Workup

  1. temperatureunder strong reflux (325 W lamp) during 7.5 hours
  2. temperatureAfter cooling
  3. filtrationfiltration
  4. washthe solution is washed with water (100 mL, 3 times)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customsome 1-fluoro-2-phthalimido-4-methyl-5-bromo-3-pentene, is used for the next step without further purification

Sources & evidence

ORD record
ord-8125cd659cb04adab63a0eb17083bc75
Source dataset
uspto-grants-1984_05
Patent number
US04446151

Reaction notes

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