N-bromobutanimide → 3-Bromo-5-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}benzonitrile

HRID 1874885Notes

Reaction equation

HRID 1874885 reaction equation
[Br: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>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br: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]([CH2:18][Br:27])[C:12]=2[F:19])[CH:9]=1)[C:5]#[N:6]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 684882443-Bromo-5-[(6-chloro-2-fluoro-3-methylphenyl)oxy]benzonitrile

Product 1

HCID 684876943-Bromo-5-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}benzonitrileYield 60.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

3-bromo-5-[(6-chloro-2-fluoro-3-methylphenyl)oxy]benzonitrile (6.05 g, 17.76 mmol) and NBS (3.16 g, 17.76 mmol) were combined in carbon tetrachloride (100 mL) with a catalytic amount of AIBN (0.146 g, 0.888 mmol) and stirred at reflux for 16 h. The reaction mixture was washed with water, dried over MgSO4, filtered and concentrated to dryness. The residue was purified on silica gel (eluted with 0 to 10% Et2O in hexanes) to give 3-bromo-5-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}benzonitrile (4.5 g, 10.73 mmol, 60.4% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.92-7.95 (m, 1H), 7.52-7.61 (m, 4H), 4.75 (s, 2H).

Workup

  1. temperatureat reflux for 16 h
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was purified on silica gel (eluted with 0 to 10% Et2O in hexanes)

Sources & evidence

ORD record
ord-7b787765a0884f3c8c8aa805e39c1241
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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