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

HRID 533999Notes

Reaction equation

HRID 533999 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CN(C=O)C.[H-].[Na+].[Br:16][C:17]1[CH:18]=[C:19]([N+]([O-])=O)[C:20]([C:23]#[N:24])=[N:21][CH:22]=1>O>[Br:16][C:17]1[CH:18]=[C:19]([O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:20]([C:23]#[N:24])=[N:21][CH:22]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 97324-FluorophenolHCID 24758Sodium hydrideHCID 27696985-Bromo-3-nitropyridine-2-carbonitrile

Product 1

HCID 669950285-Bromo-3-(4-fluorophenoxy)picolinonitrileYield 113.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A flask was charged with 4-fluorophenol (44 g, 365 mmol) and DMF (500 mL). The reaction was cooled to 0° C. Sodium hydride (16.6 g, 414 mmol) was added and stirred for 10 minutes. 5-Bromo3-nitropicolinonitrile (90 g, 395 mmol) was added and the mixture stirred at ambient temperature for 30 minutes. The reaction was poured into a flask containing water (5000 mL) and stirred for 10 minutes. The pH was adjusted to 10 to give 5-Bromo-3-(4-fluorophenoxy)picolinonitrile (121 g, 413 mmol, 105% yield) as a solid.

Workup

  1. stirringthe mixture stirred at ambient temperature for 30 minutes
  2. additionThe reaction was poured into a flask
  3. stirringstirred for 10 minutes

Sources & evidence

ORD record
ord-e22b91ff687447d9a360ee86d3de5b57
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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