Water → 5-Bromo-3-(2,6-dimethylpyridin-3-yloxy)picolinonitrile

HRID 1511023Notes

Reaction equation

HRID 1511023 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[H-].[Na+].[Br:12][C:13]1[CH:14]=[C:15]([N+]([O-])=O)[C:16]([C:19]#[N:20])=[N:17][CH:18]=1.O>CN(C=O)C>[Br:12][C:13]1[CH:14]=[C:15]([O:8][C:7]2[C:2]([CH3:1])=[N:3][C:4]([CH3:9])=[CH:5][CH:6]=2)[C:16]([C:19]#[N:20])=[N:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 707322,6-Dimethyl-3-pyridinolHCID 27696985-Bromo-3-nitropyridine-2-carbonitrile

Product 1

HCID 674864525-Bromo-3-(2,6-dimethylpyridin-3-yloxy)picolinonitrileYield 101.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. solution of 2,6-dimethylpyridin-3-ol (10 g, 81.2 mmol) in DMF (50 ml) was added sodium hydride (60% dispersion in oil, 3.4 g, 85 mmol). After 15 minutes, 5-bromo-3-nitropicolinonitrile (18.5 g, 81 mmol) was added and the mixture was allowed to warm slowly to ambient temperature. The reaction mixture was slowly added to 500 mL of rapidly stirring water. A light red solid formed and then the material formed a gum. The gum was extracted into ethyl acetate, and the organics washed with brine, dried over MgSO4 and concentrated in vacuo to afford 5-bromo-3-(2,6-dimethylpyridin-3-yloxy)picolinonitrile (25 g, 82 mmol, 101% yield).

Workup

  1. customA light red solid formed
  2. customthe material formed a gum
  3. extractionThe gum was extracted into ethyl acetate
  4. washthe organics washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df9d5f886d404ab9804c313940d032ff
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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