Sodium Hydroxide → (Z)-2-(4-chloro-2-fluoro-phenyl)-4-cyclopropyl-but-2-enenitrile

HRID 909007Notes

Reaction equation

HRID 909007 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[C:4]([F:11])[CH:3]=1.[CH:12]1([CH2:15][CH:16]=O)[CH2:14][CH2:13]1.[OH-].[Na+]>CC(O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5](/[C:6](=[CH:16]/[CH2:15][CH:12]2[CH2:14][CH2:13]2)/[C:7]#[N:8])=[C:4]([F:11])[CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2736569(4-Chloro-2-fluoro-phenyl)-acetonitrileHCID 103078492-Cyclopropylacetaldehyde

Product 1

HCID 58222867(Z)-2-(4-chloro-2-fluoro-phenyl)-4-cyclopropyl-but-2-enenitrileYield 50.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chloro-2-fluoro-benzyl cyanide (Oakwood) (3.39 g, 20.0 mmol) and cyclopropyl-acetaldehyde (Aldrich) (1.68.0 g, 20.0 mmol) in iPrOH (25 mL) was added 2 N NaOH (2.0 mL) dropwise at rt and the reaction mixture was stirred at rt overnight. The reaction mixture was diluted with EtOAc and the organic layer was separated, washed with water, brine, dried over Na2SO4 and concentrated. The residue was dried overnight under reduced pressure to afford (Z)-2-(4-chloro-2-fluoro-phenyl)-4-cyclopropyl-but-2-enenitrile (2.36 g, 50.0%) as a colorless oil which was used in the next step without further purification.

Workup

  1. customthe organic layer was separated
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was dried overnight under reduced pressure

Sources & evidence

ORD record
ord-d42bf023f270420f968cd00e202746ce
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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