4-Chlorobenzyl cyanide → (Z)-3-(3-chloro-2-fluoro-phenyl)-2-(4-chloro-phenyl)-acrylonitrile

HRID 1806707Notes

Reaction equation

HRID 1806707 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[Cl:11][C:12]1[C:13]([F:20])=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=O.C[O-].[Na+]>CO>[Cl:11][C:12]1[C:13]([F:20])=[C:14](/[CH:15]=[C:6](/[C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)\[C:7]#[N:8])[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 2415824-Chlorobenzyl cyanideHCID 7363353-Chloro-2-fluorobenzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 59249283(Z)-3-(3-chloro-2-fluoro-phenyl)-2-(4-chloro-phenyl)-acrylonitrileYield 92.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in Example 1b, 4-chlorobenzyl cyanide (8.9 g, 59 mmol) was reacted with 3-chloro-2-fluorobenzaldehyde (Oakwood) (10 g, 63 mmol), methanolic solution (25 wt %) of sodium methoxide (15 mL, 66 mmol) in methanol (300 mL) at 40° C. for 5 h to give (Z)-3-(3-chloro-2-fluoro-phenyl)-2-(4-chloro-phenyl)-acrylonitrile as a white powder (16 g, 92%).

Sources & evidence

ORD record
ord-b4630f0b4dd74b70a523d9bc5679fc50
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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