Azobisisobutyronitrile → HCID 59451576, compound

HRID 1874783

Reaction equation

HRID 1874783 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[C:13]([CH3:18])[C:12]=2[F:19])[CH:9]=1)[C:5]#[N:6].C1C(=O)N([Br:27])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:27][CH2:18][C:13]1[C:12]([F:19])=[C:11]([O:10][C:8]2[CH:7]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:9]=2)[C:5]#[N:6])[C:16]([Cl:17])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6547Azobisisobutyronitrile2×HCID 67184N-bromobutanimide2×HCID 594516403-Chloro-5-(6-chloro-2-fluoro-3-methylphenoxy)benzonitrile

Product 1

HCID 59451576HCID 59451576, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3-Chloro-5-[(6-chloro-2-fluoro-3-methylphenyl)oxy]benzonitrile (1.8 g, 6.1 mmol) was dissolved in CCl4 (200 mL). NBS (1.2 g, 6.7 mmol) and AIBN (0.63 g, 3.8 mmol) were added and the reaction mixture was placed in oil bath at 85° C. and stirred for 4 h. The reaction was monitored by TLC and more AIBN and NBS were added as necessary. The reaction was cooled, filtered and the solid washed with CCl4. The solvent was evaporated. Purification was accomplished by column chromatography (hexane/EtOAc eluent) to afford the title compound (1.8 g, 79%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.81 (s, 1H), 7.49-7.59 (m, 3H), 7.47 (d, 1H), 4.73 (s, 2H). GC-MS, 372.9 (M).

Workup

  1. customthe reaction mixture was placed in oil bath at 85° C.
  2. additionwere added as necessary
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. washthe solid washed with CCl4
  6. customThe solvent was evaporated
  7. customPurification

Sources & evidence

ORD record
ord-81e8ca9c30bc451ca73ed26f2a9a8f00
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Linked notes

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