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

HRID 1806901Notes

Reaction equation

HRID 1806901 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[C:4](C)[CH:3]=1.[Cl:12][C:13]1[C:14]([F:21])=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.[CH3:22][O-].[Na+]>CO>[Cl:12][C:13]1[C:14]([F:21])=[C:15](/[CH:16]=[C:6](/[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[C:10]([CH3:22])[CH:9]=2)\[C:7]#[N:8])[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 7363353-Chloro-2-fluorobenzaldehydeHCID 10942334Sodium MethoxideHCID 184099344-Chloro-2-methylbenzeneacetonitrile

Product 1

HCID 59249498(Z)-3-(3-chloro-2-fluoro-phenyl)-2-(4-chloro-3-methyl-phenyl)-acrylonitrileYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Step C In a manner similar to the method described in Example 1b, 4-chloro-2-methylbenzyl cyanide (1.2 g, 7.2 mmol) was reacted with 3-chloro-2-fluorobenzaldehyde (1.38 g, 8.7 mmol), methanolic solution (25 wt %) of sodium methoxide (1.82 mL, 8 mmol) in methanol (50 mL) at 50° C. for 3 h to give (Z)-3-(3-chloro-2-fluoro-phenyl)-2-(4-chloro-3-methyl-phenyl)-acrylonitrile as a white solid (2.0 g, 91%).

Sources & evidence

ORD record
ord-781bd116da1a4a7d86bb01c48071b96f
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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