Acetonitrile → 3-Amino-3-(4-fluorophenyl)acrylonitrile

HRID 2109927Notes

Reaction equation

HRID 2109927 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[C:10](#[N:12])[CH3:11].CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[NH2:7][C:6]([C:5]1[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=1)=[CH:11][C:10]#[N:12]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 145174-FluorobenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 573643293-Amino-3-(4-fluorophenyl)acrylonitrileYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-fluorobenzonitrile (5.00 g, 41.3 mmol) and acetonitrile (4.35 mL, 82.5 mmol) in toluene (100 mL) was added potassium tert-butoxide (13.9 g, 124 mmol). The mixture was stirred for 24 h, and then quenched by slow addition of aqueous sodium bicarbonate. The resulting suspension was extracted with dichloromethane (3×50 mL). The organic solution was washed with water, dried (Na2SO4), and concentrated under reduced pressure. The residue was triturated with EtOH/Et2O to afford 3-amino-3-(4-fluorophenyl)acrylonitrile (6.20 g, 93%) as a white solid. 1H NMR (300 MHz, acetone-d6) δ 4.23 (s, 1H), 6.20 (s, 2H), 7.22 (ddd, 2H), 7.71 (m, 2H).

Workup

  1. customquenched by slow addition of aqueous sodium bicarbonate
  2. extractionThe resulting suspension was extracted with dichloromethane (3×50 mL)
  3. washThe organic solution was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with EtOH/Et2O

Sources & evidence

ORD record
ord-e855b59cef424659952f173d47412078
Source dataset
uspto-grants-2009_04
Patent number
US07517878B2

Reaction notes

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