(4-Chloro-2-fluoro-phenyl)-acetonitrile → HCID 59249448, compound

HRID 1806878Notes

Reaction equation

HRID 1806878 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:14]=[CH:15][C:16]([O:21][CH3:22])=[C:17]([CH:20]=1)[CH:18]=O.C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[CH:18]/[C:17]2[CH:20]=[C:13]([Cl:12])[CH:14]=[CH:15][C:16]=2[O:21][CH3:22])/[C:9]#[N:10])=[C:4]([F:11])[CH:3]=1

Participants

5

Reactant 3

HCID 2736569(4-Chloro-2-fluoro-phenyl)-acetonitrileHCID 37183565-Chloro-2-methoxybenzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 59249448HCID 59249448, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in Example 1b, 4-chloro-2-fluorophenylacetonitrile (2.8 g, 16.6 mmol) was reacted with 5-chloro-2-methoxybenzaldehyde (Matrix) (3.4 g, 19.9 mmol), methanolic solution (25 wt %) of sodium methoxide (4.17 mL, 18 mmol) in methanol (100 mL) at 50° C. for 3 h to give (Z)-2-(4-chloro-2-fluoro-phenyl)-3-(5-chloro-2-methoxy-phenyl)-acrylonitrile as a white solid (2.0 g, 37%).

Sources & evidence

ORD record
ord-3199dd19f1624f6aa43d9d531d40b6ce
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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