4-Bromothiophene-2-carbaldehyde → HCID 59249447, compound

HRID 1806835Notes

Reaction equation

HRID 1806835 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[CH:14]=[C:15]([CH:18]=O)[S:16][CH:17]=1.C[O-].[Na+]>CO>[Br:12][C:13]1[CH:14]=[C:15](/[CH:18]=[C:8](/[C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[F:11])\[C:9]#[N:10])[S:16][CH:17]=1

Participants

5

Reactant 3

HCID 877924-Bromothiophene-2-carbaldehydeHCID 2736569(4-Chloro-2-fluoro-phenyl)-acetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 59249447HCID 59249447, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in Example 1b, 4-chloro-2-fluorophenylacetonitrile (4.05 g, 24 mmol) was reacted with 4-bromo-2-thiophenecarboxaldehyde (Aldrich) (6.08 g, 29 mmol), methanolic solution (25 wt %) of sodium methoxide (6 mL, 26 mmol) in methanol (90 mL) at 50° C. for 3 h to give (Z)-3-(4-bromo-thiophen-2-yl)-2-(4-chloro-2-fluoro-phenyl)-acrylonitrile as a light yellow solid (5.2 g, 64%).

Sources & evidence

ORD record
ord-2992a62fd4234bab8b41f8499f16029b
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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