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

HRID 1806792Notes

Reaction equation

HRID 1806792 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[C:4]([O:11][CH3:12])[CH:3]=1.[Cl:13][C:14]1[C:15]([F:22])=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O.C[O-].[Na+]>CO>[Cl:13][C:14]1[C:15]([F:22])=[C:16](/[CH:17]=[C:6](/[C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][C:4]=2[O:11][CH3:12])\[C:7]#[N:8])[CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 7363353-Chloro-2-fluorobenzaldehydeHCID 10942334Sodium MethoxideHCID 223275242-(4-Chloro-2-methoxyphenyl)acetonitrile

Product 1

HCID 59249520(Z)-3-(3-chloro-2-fluoro-phenyl)-2-(4-chloro-2-methoxy-phenyl)-acrylonitrileYield 65.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Step C In a manner similar to the method described in Example 1b, 4-chloro-2-methoxybenzyl cyanide (1.8 g, 10 mmol) was reacted with 3-chloro-2-fluorobenzaldehyde (2 g, 13 mmol), methanolic solution (25 wt %) of sodium methoxide (15 mL, 66 mmol) in methanol (50 mL) at 50° C. for 2 h to give (Z)-3-(3-chloro-2-fluoro-phenyl)-2-(4-chloro-2-methoxy-phenyl)-acrylonitrile as a white powder (2.1 g, 65%).

Sources & evidence

ORD record
ord-e454ae7f9cb44653a314330d89ef778c
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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