Azobisisobutyronitrile → HCID 18700073, compound

HRID 1740584Notes

Reaction equation

HRID 1740584 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-butyl-carbonyl)-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-butylcarbonyl)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-9771b835e9c8491784b2ecbe032cd8e6
Source dataset
uspto-grants-1999_10
Patent number
US05968938

Reaction notes

Loading…