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

HRID 1806831Notes

Reaction equation

HRID 1806831 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[C:4]([F:11])[CH:3]=1.[Cl:12][C:13]1[CH:20]=[CH:19][C:16](C=O)=[CH:15][C:14]=1[F:21].[CH3:22][O-].[Na+]>CO>[Cl:12][C:13]1[CH:20]=[C:19](/[CH:22]=[C:8](/[C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[F:11])\[C:9]#[N:10])[CH:16]=[CH:15][C:14]=1[F:21]

Participants

5

Reactant 3

HCID 27249854-Chloro-3-FluorobenzaldehydeHCID 2736569(4-Chloro-2-fluoro-phenyl)-acetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 59249591(Z)-3-(3-chloro-4-fluoro-phenyl)-2-(4-chloro-2-fluoro-phenyl)-acrylonitrileYield 50.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in Example 1b, 4-chloro-2-fluorophenylacetonitrile (3.3 g, 19 mmol) was reacted with 4-chloro-3-fluoro-benzaldehyde (Aldrich) (3.65 g, 23 mmol), methanolic solution (25 wt %) of sodium methoxide (4.8 mL, 21 mmol) in methanol (90 mL) at 50° C. for 3 h to give (Z)-3-(3-chloro-4-fluoro-phenyl)-2-(4-chloro-2-fluoro-phenyl)-acrylonitrile as a white powder (3 g, 50%).

Sources & evidence

ORD record
ord-580d51b62fe94d98ae391a06f49a37ea
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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