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

HRID 1806780Notes

Reaction equation

HRID 1806780 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[CH2:4][C:5]#[N:6].[Cl:12][C:13]1[C:14]([F:21])=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.C[O-].[Na+]>CO>[Cl:12][C:13]1[C:14]([F:21])=[C:15](/[CH:16]=[C:4](/[C:3]2[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:2]=2[Cl:1])\[C:5]#[N:6])[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 805662,4-DichlorophenylacetonitrileHCID 7363353-Chloro-2-fluorobenzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 59249401(Z)-3-(3-chloro-2-fluoro-phenyl)-2-(2,4-dichloro-phenyl)-acrylonitrileYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in Example 1b, 2,4-dichlorobenzyl cyanide (6 g, 32 mmol) was reacted with 3-chloro-2-fluorobenzaldehyde (6 g, 38 mmol), methanolic solution (25 wt %) of sodium methoxide (30 mL, 131 mmol) in methanol (200 mL) at 50° C. for 3 h to give (Z)-3-(3-chloro-2-fluoro-phenyl)-2-(2,4-dichloro-phenyl)-acrylonitrile as a white powder (7 g, 67%).

Sources & evidence

ORD record
ord-f50bbac2a7bd4a349f120e0f4cf2e8ef
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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