Water → 5-Bromo-3-(4-fluorophenoxy)picolinonitrile

HRID 335119

Reaction equation

HRID 335119 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[Br:11][C:12]1[CH:13]=[C:14]([N+]([O-])=O)[C:15]([C:18]#[N:19])=[N:16][CH:17]=1.O>CN(C=O)C>[Br:11][C:12]1[CH:13]=[C:14]([O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:15]([C:18]#[N:19])=[N:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 97324-FluorophenolHCID 24758Sodium hydrideHCID 27696985-Bromo-3-nitropyridine-2-carbonitrile

Product 1

HCID 669950285-Bromo-3-(4-fluorophenoxy)picolinonitrileYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-fluorophenol (0.49 g, 4.4 mmol) in DMF (10 mL) cooled to 0° C. was added 60% sodium hydride (0.19 g, 4.8 mmol) was added and the reaction was warmed to ambient temperature. 5-Bromo-3-nitropicolinonitrile (1.0 g, 4.4 mmol, solution in 5 mL DMF) and stirred for 3 hours. Poured into water, filtered, washed with water, and dried to yield the title compound (1.0 g, 78%).

Workup

  1. additionwas added
  2. filtrationfiltered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-b58cd363cc784bfa97268f8ce6c04e6e
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Linked notes

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