Benzoyl Peroxide → HCID 19698381, compound

HRID 862572Notes

Reaction equation

HRID 862572 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[O:11][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13])([O-:3])=[O:2].BrN1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:45]1(=[O:55])[NH:49][C:48](=[O:50])[C:47]2=[CH:51][CH:52]=[CH:53][CH:54]=[C:46]12.[K]>C(Cl)(Cl)(Cl)Cl.[Cl-].[Na+].O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:49]2[C:48](=[O:50])[C:47]3=[CH:51][CH:52]=[CH:53][CH:54]=[C:46]3[C:45]2=[O:55])=[CH:6][C:5]=1[O:11][S:12]([C:15]([F:18])([F:16])[F:17])(=[O:14])=[O:13])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 19698375HCID 19698375, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 19698381HCID 19698381, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 4-nitro-3-trifluoromethanesulfonyloxytoluene (5.7 g, 20 mmol), N-bromosuccinimide (5.7 g, 32 mmol), and benzoyl peroxide (1 g) in carbon tetrachloride (75 mL) was refluxed for 18 h. The insoluble material formed was removed by filtration and the filtrate was concentrated. The residue was dissolved in DMF (40 mL) and potassium phthalimide (2.6 g, 14 mmol) was added. The mixture was stirred for 5 h at room temperature, poured into brine, and extracted with a 1:1 mixture of toluene and ethyl acetate. The organic layers were washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 9:1 to 1:1 hexane/ethyl acetate to give 3.4 g of the title compound (39%).

Workup

  1. temperaturewas refluxed for 18 h
  2. customThe insoluble material formed
  3. customwas removed by filtration
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in DMF (40 mL)
  6. extractionextracted with a 1:1 mixture of toluene and ethyl acetate
  7. washThe organic layers were washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography with 9:1 to 1:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-a96ca7db579142ef886c23c39ecd7025
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

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