Azobisisobutyronitrile → HCID 22031053, compound

HRID 1792509Notes

Reaction equation

HRID 1792509 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([CH3:12])[CH:3]=1.BrN1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[F:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][CH:35]=1>CO.C(N(CC)CC)C.C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:10][CH:11]=1)[C:6](=[O:8])[N:39]([CH2:38][C:37]1[CH:40]=[CH:41][C:34]([F:33])=[CH:35][CH:36]=1)[CH2:12]2

Participants

8

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimide2×HCID 673264-FluorobenzylamineHCID 22031226Methyl 4-bromo-2-methylbenzoate

Product 1

HCID 22031053HCID 22031053, compoundYield 34.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 5943Carbon TetrachlorideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 458 mg methyl 4-bromo-2-methylbenzoate, 427 mg N-bromosuccinimide, 25 mg α,α′-azobisisobutyronitrile and 10 mL carbon tetrachloride was heated for 30 minutes under reflux. 50 mg N-bromosuccinimide was added thereto, and the mixture was further heated for 30 minutes under reflux. The reaction solution was cooled, insolubles were filtered off, and the filtrate was evaporated. 773 mg crude product of methyl 4-bromo-2-bromomethyl benzoate was obtained as a pale yellow oil. A mixture of this compound, 546 mg 4-fluorobenzyl amine, 0.34 mL triethylamine and 10 mL methanol was heated for 2 days under reflux. The reaction solution was cooled, and the precipitated crystals were collected by filtration and dried under reduced pressure with a vacuum pump, to give 219 mg of the title compound as pale brown crystals.

Workup

  1. temperaturewas heated for 30 minutes
  2. temperatureunder reflux
  3. temperaturethe mixture was further heated for 30 minutes
  4. temperatureunder reflux
  5. temperatureThe reaction solution was cooled
  6. filtrationinsolubles were filtered off
  7. customthe filtrate was evaporated
  8. custom773 mg crude product of methyl 4-bromo-2-bromomethyl benzoate was obtained as a pale yellow oil
  9. temperaturewas heated for 2 days
  10. temperatureunder reflux
  11. temperatureThe reaction solution was cooled
  12. filtrationthe precipitated crystals were collected by filtration
  13. customdried under reduced pressure with a vacuum pump

Sources & evidence

ORD record
ord-505d1b14e7004be6bcec09611ab16457
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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