Water → HCID 73877104, compound

HRID 749567Notes

Reaction equation

HRID 749567 reaction equation
Br[CH:2]([C:5]1[CH:22]=[CH:21][C:8]([CH2:9][C:10]([CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18])([C:13]#[N:14])[C:11]#[N:12])=[CH:7][CH:6]=1)[CH2:3][Br:4].CC(C)([O-])C.[K+].O>CN(C)C=O>[Br:4][CH:3]=[CH:2][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][C:10]([CH2:15][CH2:16][C:17]([F:18])([F:19])[F:20])([C:13]#[N:14])[C:11]#[N:12])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 22235062HCID 22235062, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 73877104HCID 73877104, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

First, 0.2 g of (2-(4-(1,2-dibromoethyl)benzyl)-2-(3,3,3-trifluoropropyl)malononitrile (the present compound (43)) was dissolved in 5 ml of N,N-dimethylformamide, to which 0.1 g of potassium t-butoxide was added, while stirring under ice cooling. After stirring for 5 hours at room temperature, water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was successively washed with water, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.05 g of 2-(4-(2-bromovinyl)benzyl)-2-(3,3,3-trifluoropropyl)malononitrile (the present compound (58)).

Workup

  1. additionwas added
  2. stirringAfter stirring for 5 hours at room temperature
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was successively washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-60c347c5dae94e8db37aaec63208feab
Source dataset
uspto-grants-2008_07
Patent number
US07402691B2

Reaction notes

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