3,4-Dichlorobenzaldehyde → (Z)-2-(4-chloro-2-fluoro-phenyl)-3-(3,4-dichloro-phenyl)-acrylonitrile

HRID 1806827Notes

Reaction equation

HRID 1806827 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][C:20]=1[Cl:21])[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][C:20]([Cl:21])=[C:13]([Cl:12])[CH:14]=2)/[C:9]#[N:10])=[C:4]([F:11])[CH:3]=1

Participants

5

Reactant 3

HCID 227103,4-DichlorobenzaldehydeHCID 2736569(4-Chloro-2-fluoro-phenyl)-acetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 59249615(Z)-2-(4-chloro-2-fluoro-phenyl)-3-(3,4-dichloro-phenyl)-acrylonitrileYield 76.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in Example 1b, 4-chloro-2-fluorophenyl acetonitrile (4.5 g, 26 mmol) was reacted with 3,4-dichlorobenzaldehyde (Aldrich) (5.5 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-(3,4-dichloro-phenyl)-acrylonitrile as a white powder (6.5 g, 76%).

Sources & evidence

ORD record
ord-541d29bdcdb447768f6c27ffb4562d56
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

Loading…