Acrylonitrile → Ethyl 4-cyano-2,2-bis(4-fluorophenyl)butanoate

HRID 1667168Notes

Reaction equation

HRID 1667168 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[O-]CC.[Na+].[C:25](#[N:28])[CH:26]=[CH2:27]>O1CCOCC1>[C:25]([CH2:26][CH2:27][C:8]([C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1)([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])#[N:28]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 2723922Sodium ethoxideHCID 54751768Ethyl 2,2-bis(4-fluorophenyl)acetate

Product 1

HCID 67358414Ethyl 4-cyano-2,2-bis(4-fluorophenyl)butanoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of ethyl 2,2-bis(4-fluorophenyl)acetate (1.55 g, 5.64 mmol) in anhydrous dioxane (10 mL) was added sodium ethoxide (0.38 g, 5.61 mmol), and the reaction was stirred at a temperature between 40-50° C. for 30 minutes. Acrylonitrile (0.35 mL, 5.61 mmol) was added dropwise with stirring, and the reaction was heated at 60-70° C. for an additional 1 hour. The dioxane was removed in vacuo, and the residue was taken up in ether, washed with water and brine, dried with MgSO4, filtered and concentrated. Silica gel chromatography eluting with a gradient of 3% to 10% ethyl acetate/hexane gave the title compound. MS (DCI) m/z 342 (M+NH4)+.

Workup

  1. stirringwith stirring
  2. temperaturethe reaction was heated at 60-70° C. for an additional 1 hour
  3. customThe dioxane was removed in vacuo
  4. washwashed with water and brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washSilica gel chromatography eluting with a gradient of 3% to 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-10fc9cf6facd4e34ae13fa47ee1626c1
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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