Azobisisobutyronitrile → HCID 18700073, compound

HRID 2289329Notes

Reaction equation

HRID 2289329 reaction equation
[C:1]([C:5]([N:7]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])[CH:15]=1)[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9])=[O:6])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:34])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[C:10]([C:8]([N:7]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][Br:34])=[C:16]([O:21][CH2:22][C:23]([F:24])([F:25])[F:26])[CH:15]=1)[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[O:6])=[O:9])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 18700188HCID 18700188, compound

Product 1

HCID 18700073HCID 18700073, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 4-(N,N-di-(tert-butylcarbonyl)amino)-2-(2,2,2-trifluoroethoxy)toluene (2.0 g, 5.0 mmol) from Step 3 above in CCl4 (75 mL) was added NBS (0.90 g, 5.0 mmol) and AIBN (0.2 g, 1.2 mmol). The mixture was refluxed for 2 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc (100 mL) and saturated aqueous NaHCO3 (2×50 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using a gradient elution of 5-15% EtOAc:hexanes to give 4-(N,N-di-(tert-butyl-carbonyl)amino)-2-(2,2,2-trifluoroethoxy)benzyl bromide as a colorless gum (TLC Rf =0.50 (15% EtOAc:hexanes)).

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between EtOAc (100 mL) and saturated aqueous NaHCO3 (2×50 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by pressurized silica gel column chromatography
  8. washa gradient elution of 5-15% EtOAc

Sources & evidence

ORD record
ord-80c2afcf2dad40c28c7c5a8555795138
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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