Benzeneacetonitrile, 4-bromo- → HCID 59249234, compound

HRID 1806772Notes

Reaction equation

HRID 1806772 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[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>[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[CH:15]/[C:14]2[CH:17]=[CH:18][CH:19]=[C:12]([Cl:11])[C:13]=2[F:20])/[C:9]#[N:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 27914Benzeneacetonitrile, 4-bromo-HCID 7363353-Chloro-2-fluorobenzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 59249234HCID 59249234, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in Example 1b, 4-bromophenylacetonitrile (Aldrich) (4.5 g, 23 mmol) was reacted with 3-chloro-2-fluorobenzaldehyde (5.2 g, 33 mmol), methanolic solution (25 wt %) of sodium methoxide (15 mL, 66 mmol) in methanol (150 mL) at 50° C. for 3 h to give (Z)-2-(4-bromo-phenyl)-3-(3-chloro-2-fluoro-phenyl)-acrylonitrile as a white powder (7.8 g, 100%).

Sources & evidence

ORD record
ord-5155e53fd60a4570be90c0d7e3862676
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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