Dimethylformamide → 5-Fluoro-4-(trifluoromethyl)-2-pyridinecarbonitrile

HRID 1880726Notes

Reaction equation

HRID 1880726 reaction equation
[CH3:1][N:2](C)C=O.Br[C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[C:10]([F:17])=[CH:9][N:8]=1>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[F:17][C:10]1[C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:7]([C:1]#[N:2])=[N:8][CH:9]=1

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 56604232HCID 56604232, compound

Product 1

HCID 595703465-Fluoro-4-(trifluoromethyl)-2-pyridinecarbonitrile

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To 12 ml of N,N-dimethylformamide were added 0.8 g of 2-bromo-5-fluoro-4-trifluoromethylpyridine, 1.41 g of zinc cyanide and 0.28 g of tetrakistriphenylphosphinepalladium, and the mixture was stirred at 95° C. for 14 hours. After allowing to cool, the reaction solution was poured into water, and the resultant solution was extracted with diethyl ether three times, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.5 g of 5-fluoro-4-trifluoromethylpyridine-2-carbonitrile.

Workup

  1. temperatureto cool
  2. extractionthe resultant solution was extracted with diethyl ether three times
  3. washwashed with an aqueous saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f56b6dffddac41eb83ece9753e2dc291
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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