Azobisisobutyronitrile → HCID 59557730, compound

HRID 2403716Notes

Reaction equation

HRID 2403716 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:17])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[O:9])[CH:7]=1.C1C(=O)N([Br:25])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:17])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][Br:25])=[CH:12][CH:11]=2)=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 23560508HCID 23560508, compound

Product 1

HCID 59557730HCID 59557730, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (5-bromo-2-chlorophenyl)(p-tolyl)methanone (intermediate AG) (16 g, 48.9 mmol) in CCl4 (80 mL), NBS (10.08 g, 57 mmol) and AIBN (0.848 g) was added. Then the mixture was heated to 90° C. After 3 h, CCl4 was removed under reduced pressure. The residue was dissolved in CH2Cl2 and the solution was washed 1× with HCl (1M) and 2× with brine prior to drying over Na2SO4. Solvent was removed under reduced pressure to obtain crude intermediate AH (20.75 g).

Workup

  1. customCCl4 was removed under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washthe solution was washed 1× with HCl (1M) and 2× with brine
  4. dry with materialto drying over Na2SO4
  5. customSolvent was removed under reduced pressure
  6. customto obtain crude intermediate AH (20.75 g)

Sources & evidence

ORD record
ord-ea957ad3de8d4398b76958bdb4320ba7
Source dataset
uspto-grants-2014_08
Patent number
US08802637B2

Reaction notes

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