Benzoyl Peroxide → 1-Fluoro-2-phthalimido-5-bromo-3-pentene

HRID 1904101Notes

Reaction equation

HRID 1904101 reaction equation
[F:1][CH2:2][CH:3]([N:7]1[C:11](=[O:12])[C:10]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]2[C:8]1=[O:17])[CH:4]=[CH:5][CH3:6].[Br:18]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:7]1[C:8](=[O:17])[C:9]2=[CH:16][CH:15]=[CH:14][CH:13]=[C:10]2[C:11]1=[O:12])[CH:4]=[CH:5][CH2:6][Br:18]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 545341051-Fluoro-2-phthalimido-3-pentene

Product 1

HCID 544810491-Fluoro-2-phthalimido-5-bromo-3-pentene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1-fluoro-2-phthalimido-3-pentene (800 mg, 3.4 mmoles) prepared as in Step C above, N-bromosuccinimide (612 mg. 3.4 mmoles), carbon tetrachloride (30 mL) and a few mg of benzoyl peroxide is heated under strong reflux during irradiation with a lamp (325 W) during one hour. After washing with water the organic phase is dried over magnesium sulfate and then concentrated under reduced pressure to yield 1-fluoro-2-phthalimido-5-bromo-3-pentene as a slightly yellow oil (1.06 g, quantitative yield).

Workup

  1. temperatureunder strong reflux during irradiation with a lamp (325 W) during one hour
  2. washAfter washing with water the organic phase
  3. dry with materialis dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0788fea1dac54205b5eac8f7cf3c7bfc
Source dataset
uspto-grants-1984_03
Patent number
US04439619

Reaction notes

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