(4-Chloro-2-fluoro-phenyl)-acetonitrile → (Z)-3-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-phenyl}-2-(4-chloro-2-fluoro-phenyl)-acrylonitrile

HRID 1806874Notes

Reaction equation

HRID 1806874 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.[C:12]([Si:16]([CH3:31])([CH3:30])[O:17][CH2:18][CH2:19][O:20][C:21]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:22]=1[CH:23]=O)([CH3:15])([CH3:14])[CH3:13].C[O-].[Na+]>CO>[C:12]([Si:16]([CH3:31])([CH3:30])[O:17][CH2:18][CH2:19][O:20][C:21]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:22]=1/[CH:23]=[C:8](/[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[F:11])\[C:9]#[N:10])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 2736569(4-Chloro-2-fluoro-phenyl)-acetonitrileHCID 10942334Sodium MethoxideHCID 575659162-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-benzaldehyde

Product 1

HCID 59249244(Z)-3-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-phenyl}-2-(4-chloro-2-fluoro-phenyl)-acrylonitrileYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Step B In a manner similar to the method described in Example 1b, 4-chloro-2-fluorophenylacetonitrile (1.7 g, 10 mmol) was reacted with 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-benzaldehyde (3.8 g, 12.5 mmol), methanolic solution (25 wt %) of sodium methoxide (2.5 mL, 11 mmol) in methanol (60 mL) at 50° C. for 3 h to give (Z)-3-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-phenyl}-2-(4-chloro-2-fluoro-phenyl)-acrylonitrile as a yellow oil (4.5 g, 80%).

Sources & evidence

ORD record
ord-f0ac5fe5ccbd4f159c884e93a450c080
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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