3-Chlorobenzaldehyde → (Z)-2-(4-Chloro-2-fluoro-phenyl)-3-(3-chloro-phenyl)-acrylonitrile

HRID 1806813Notes

Reaction equation

HRID 1806813 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[C:4]([F:11])[CH:3]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[CH:16]/[C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([Cl:12])[CH:14]=2)/[C:9]#[N:10])=[C:4]([F:11])[CH:3]=1

Participants

5

Reactant 3

HCID 114773-ChlorobenzaldehydeHCID 2736569(4-Chloro-2-fluoro-phenyl)-acetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 59249419(Z)-2-(4-Chloro-2-fluoro-phenyl)-3-(3-chloro-phenyl)-acrylonitrileYield 85.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in Example 1b, 4-chloro-2-fluorophenylacetonitrile (4.5 g, 26 mmol) was reacted with 3-chlorobenzaldehyde (Aldrich) (4.4 g, 32 mmol), methanolic solution (25 wt %) of sodium methoxide (6.6 mL, 29 mmol) in methanol (150 mL) at 50° C. for 3 h to give (Z)-2-(4-Chloro-2-fluoro-phenyl)-3-(3-chloro-phenyl)-acrylonitrile as a white powder (6.5 g, 84%).

Sources & evidence

ORD record
ord-a682282eb98e44d29c61e5b3cca0773b
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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