Azobisisobutyronitrile → HCID 68487765, compound

HRID 1875057Notes

Reaction equation

HRID 1875057 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([F:9])[C:3]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1C(=O)N([Br:24])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:24][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:4]=1[F:9]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 18440077HCID 18440077, compound

Product 1

HCID 68487765HCID 68487765, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1-chloro-3-fluoro-4-methyl-2-(phenyloxy)benzene (0.500 g, 2.113 mmol), NBS (0.414 g, 2.324 mmol) and AIBN (0.017 g, 0.106 mmol) in carbon tetrachloride (8 mL) was heated at reflux overnight. The reaction mixture was cooled to RT and filtered through Celite. The solvent was evaporated. Chromatography of the residue gave the desired product (0.058 g, 9%) as a white solid. 1H NMR (400 MHz, chloroform-d) δ ppm 7.27-7.35 (m, 3H), 7.18-7.27 (m, 2H), 7.05-7.11 (m, 1H), 6.89 (d, 2H), 4.30-4.59 (m, 2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. filtrationfiltered through Celite
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a0c207fe15cb44ce839f52c3015f6ced
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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