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

HRID 1806802Notes

Reaction equation

HRID 1806802 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[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O.C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:10]=[CH:9][C:5](/[C:6](=[CH:17]/[C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([Cl:13])[CH:15]=2)/[C:7]#[N:8])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 114773-ChlorobenzaldehydeHCID 10942334Sodium MethoxideHCID 223275242-(4-Chloro-2-methoxyphenyl)acetonitrile

Product 1

HCID 59249601(Z)-2-(4-chloro-2-methoxy-phenyl)-3-(3-chloro-phenyl)-acrylonitrileYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in Example 1b, 4-chloro-2-methoxybenzyl cyanide (2 g, 10 mmol) prepared in Example 58a Step B was reacted with 3-chlorobenzaldehyde (2 g, 14 mmol), methanolic solution (25 wt %) of sodium methoxide (15 mL, 66 mmol) in methanol (50 mL) at 50° C. for 5 h to give (Z)-2-(4-chloro-2-methoxy-phenyl)-3-(3-chloro-phenyl)-acrylonitrile as a white powder (1.9 g, 63%).

Sources & evidence

ORD record
ord-d43e7a20002c4c77a8df9cb336d57812
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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