N-bromobutanimide → HCID 86644895, compound

HRID 1874919Notes

Reaction equation

HRID 1874919 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([O:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[C:13]([CH3:18])[C:12]=2[F:19])[N:3]=1.C1C(=O)N([Br:27])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:27][CH2:18][C:13]1[C:12]([F:19])=[C:11]([O:10][C:4]2[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=[C:2]([Cl:1])[N:3]=2)[C:16]([Cl:17])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 866448942-Chloro-6-[(6-chloro-2-fluoro-3-methylphenyl)oxy]-4-pyridinecarbonitrile

Product 1

HCID 86644895HCID 86644895, compoundYield 57.2%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

2-chloro-6-[(6-chloro-2-fluoro-3-methylphenyl)oxy]-4-pyridinecarbonitrile (3.65 g, 12.28 mmol) and NBS (2.187 g, 12.28 mmol) were combined in carbon tetrachloride (100 mL) with a catalytic amount of AIBN (0.101 g, 0.614 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 by chromatography on 120 g silica gel eluted with 0% to 10% Et2O in hexanes to give the desired product, 2-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}-6-chloro-4-pyridinecarbonitrile (2.64 g, 7.02 mmol, 57.2% yield), as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm (8.01 (s, 1H), 7.96 (s, 1H), 7.50-7.62 (m, 2H), 4.75 (s, 2H). LC-MS (ES+) m/z 374.98, 377.01, 379.03 [M+H].

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 by chromatography on 120 g silica gel
  7. washeluted with 0% to 10% Et2O in hexanes

Sources & evidence

ORD record
ord-c47caaf6356f425794ab8e771e5bbf48
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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