Nitromethane → (E)-5-fluoro-2-(2-nitrovinyl)benzo[b]thiophene

HRID 1843960Notes

Reaction equation

HRID 1843960 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]2[S:6][C:7]([CH:9]=O)=[CH:8][C:4]=2[CH:3]=1.[N+:13]([CH3:16])([O-:15])=[O:14].[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:12]=[CH:11][C:5]2[S:6][C:7](/[CH:9]=[CH:16]/[N+:13]([O-:15])=[O:14])=[CH:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 497574655-Fluoro-1-benzothiophene-2-carbaldehyde

Product 1

HCID 66801961(E)-5-fluoro-2-(2-nitrovinyl)benzo[b]thiopheneYield 57.14%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using an analogous procedure and workup as described in example 1, for the preparation of Intermediate I-1a above, 5-fluorobenzo[b]thiophene-2-carbaldehyde (1.7 g, 9.444 mmol) was reacted with nitro methane (576.11 mg, 9.444 mmol), 10N NaOH (396.64 mg, 9.916 mmol) and ethanol (25 mL) at 0° C. for 2 hours to afford 1.2 g of the product (57.14% yield).

Sources & evidence

ORD record
ord-33c8bf52991a4acc8df1e61937feb3bf
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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