Allyl bromide → 4-[2,2,2-Trifluoro-1-(2-propenyloxy)ethyl]pyridine-2-carbonitrile

HRID 1880766Notes

Reaction equation

HRID 1880766 reaction equation
[F:1][C:2]([F:14])([F:13])[CH:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[CH:6]=1)[OH:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH:23]=[CH2:24].[Cl-].[NH4+]>CN(C)C=O>[F:14][C:2]([F:1])([F:13])[CH:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[CH:6]=1)[O:4][CH2:24][CH:23]=[CH2:22]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 595703134-(2,2,2-Trifluoro-1-hydroxyethyl)pyridine-2-carbonitrile

Product 1

HCID 595703774-[2,2,2-Trifluoro-1-(2-propenyloxy)ethyl]pyridine-2-carbonitrileYield 28.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5 ml of dimethylformamide were added 0.5 g of 4-(2,2,2-trifluoro-1-hydroxyethyl)pyridine-2-carbonitrile, 0.45 g of potassium carbonate and 0.39 g of 3-bromo-1-propene, and the mixture was stirred at room temperature for 20 hours. Thereafter, an aqueous saturated ammonium chloride solution was added to the reaction solution, the resultant solution was extracted with ethyl acetate, and the organic layers were combined, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.17 g of 4-[2,2,2-trifluoro-1-(2-propenyloxy)ethyl]pyridine-2-carbonitrile.

Workup

  1. extractionthe resultant solution was extracted with ethyl acetate
  2. dry with materialdried with anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-40f2f834b7c9493993c9bc08e8bf5b89
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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