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

HRID 1806809Notes

Reaction equation

HRID 1806809 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.[Br:12][C:13]1[C:14]([F:21])=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.C[O-].[Na+]>CO>[Br:12][C:13]1[C:14]([F:21])=[C:15](/[CH:16]=[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:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 2736569(4-Chloro-2-fluoro-phenyl)-acetonitrileHCID 10942334Sodium MethoxideHCID 220193613-Bromo-2-fluorobenzaldehyde

Product 1

HCID 59249486(Z)-3-(3-bromo-2-fluoro-phenyl)-2-(4-chloro-2-fluoro-phenyl)-acrylonitrileYield 79.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in Example 1b, 4-chloro-2-fluorophenylacetonitrile (1.39 g, 8.2 mmol) was reacted with 3-bromo-2-fluorobenzaldehyde (Apollo) (2 g, 9.9 mmol), methanolic solution (25 wt %) of sodium methoxide (2 g, 9 mmol) in methanol (40 mL) at 50° C. for 3 h to give (Z)-3-(3-bromo-2-fluoro-phenyl)-2-(4-chloro-2-fluoro-phenyl)-acrylonitrile as a white powder (2.3 g, 79%).

Sources & evidence

ORD record
ord-f8d99db2004b4a019c945d7c356767d0
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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