Azobisisobutyronitrile → HCID 67255008, compound

HRID 1947865Notes

Reaction equation

HRID 1947865 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C1C(=O)N([Br:31])C(=O)C1.N(C(C)(C)C#N)=NC(C)(C)C#N>FC(F)(F)C1C=CC=CC=1>[C:13]([O:12][C:10]([N:9]([C:3]1[CH:4]=[CH:5][C:6]([CH2:8][Br:31])=[CH:7][C:2]=1[Br:1])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:11])([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 67254193HCID 67254193, compound2×

Product 1

HCID 67255008HCID 67255008, compound

Reagents, catalysts & solvents 1

HCID 7368(Trifluoromethyl)benzeneSolvent

Procedure

A solution of di-tert-butyl (2-bromo-4-methylphenyl)imidodicarbonate (Compound 108C, 5.0 g, 13 mmol), NBS (2.56 g, 14.2 mmol) and 2,2′-Azo-bis-isobutyronitrile (0.217 g, 1.29 mmol) in α,α,α-trifluorotoluene (16 mL) was heated at 80° C. under an atmosphere of nitrogen for 3 h. Solvent was removed in vacuo and the residue was partitioned between EtOAc and water and separated. The aqueous was extracted with EtOAc (3×) and the combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated to afford the title compound. 1H NMR (400 MHz, chloroform-d) δ 7.64 (d, J=1.77 Hz, 1H), 7.34 (dd, J=2.02, 8.08 Hz, 1H), 7.19 (d, J=8.08 Hz, 1H), 4.44 (s, 2H), 1.41 (s, 18H); MS (ES+): m/z: N/A [MH+]. HPLC: tR=1.83 min (UPLC TOF MS: polar—3 min).

Workup

  1. customSolvent was removed in vacuo
  2. customthe residue was partitioned between EtOAc and water
  3. customseparated
  4. extractionThe aqueous was extracted with EtOAc (3×)
  5. washthe combined organic fractions were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-150657d999a44084b6afd6cd173ba658
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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