N-Bromosuccinamide → HCID 13958751, compound

HRID 255918Notes

Reaction equation

HRID 255918 reaction equation
[C:1]1(=[O:16])[N:5]([CH2:6]/[C:7](/[CH3:10])=[CH:8]/[F:9])[C:4](=[O:11])[C:3]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:2]12.[Br:17]NC(=O)CCC(N)=O>C(Cl)(Cl)(Cl)Cl>[F:9]/[CH:8]=[C:7](\[CH2:10][Br:17])/[CH2:6][N:5]1[C:4](=[O:11])[C:3]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:2]2[C:1]1=[O:16]

Participants

4

Reactant 2

HCID 9834204N-BromosuccinamideHCID 13958749HCID 13958749, compound

Product 1

HCID 13958751HCID 13958751, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1-phthalimido-2-methyl-3-fluoro-2-propene (prepared in Step E) (2.09 g) and N-bromosuccinamide (1.78 g) in carbon tetrachloride (100 ml) was refluxed for 45 min. The cooled mixture is filtered and the filtrate is washed with water, dried and evaporated to leave an almost colorless oil. Chromatography (silica; 20% ether in light petroleum) followed by recrystallization of the major fractions from EtOAc/light petroleum gives:

Workup

  1. temperaturewas refluxed for 45 min
  2. filtrationThe cooled mixture is filtered
  3. washthe filtrate is washed with water
  4. customdried
  5. customevaporated
  6. customto leave an almost colorless oil
  7. customChromatography (silica; 20% ether in light petroleum) followed by recrystallization of the major fractions from EtOAc/light petroleum
  8. customgives

Sources & evidence

ORD record
ord-6bd9c27fd4cc44f7aee7ac57db43ae15
Source dataset
uspto-grants-1987_10
Patent number
US04699928

Reaction notes

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