N-bromobutanimide → Methyl 5-phthalimidomethyl-2-nitrobenzoate

HRID 862598Notes

Reaction equation

HRID 862598 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].BrN1C(=O)CCC1=O.[C:23]1(=[O:33])[NH:27][C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12.[K]>C(Cl)(Cl)(Cl)Cl.[Cl-].[Na+].O.N(C(C)(C)C#N)=NC(C)(C)C#N>[C:23]1(=[O:33])[N:27]([CH2:1][C:2]2[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=2)[C:7]([O:9][CH3:10])=[O:8])[C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12

Participants

7

Reactant 3

HCID 67184N-bromobutanimideHCID 3314122Methyl 5-methyl-2-nitrobenzoateHCID 24194345Phthalimide potassium salt

Product 1

HCID 19698369Methyl 5-phthalimidomethyl-2-nitrobenzoateYield 130.6%

Reagents, catalysts & solvents 3

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 5-methyl-2-nitrobenzoate (35.0 g, 179 mmol), N-bromosuccinimide (33.5 g, 188 mmol), and azobisisobutyronitrile (500 mg) in carbon tetrachloride (450 mL) was refluxed for 14 h. The insoluble material formed was removed by filtration and the filtrate was concentrated. The residue was dissolved in DMF (300 mL) and potassium phthalimide (19.41 g, 45 mmol) was added. The mixture was stirred for 2 h at 50° C., 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 4:1 to 2:1 hexane/ethyl acetate to give 20.0 g of the title compound (33%).

Workup

  1. temperaturewas refluxed for 14 h
  2. customThe insoluble material formed
  3. customwas removed by filtration
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in DMF (300 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 4:1 to 2:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-448899815c6c4c8e8c828bd8678dbe6d
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

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