Nitromethane → 2-Bromo-5-(2-nitro-vinyl)-thiophene

HRID 1843854Notes

Reaction equation

HRID 1843854 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.[N+:9]([CH3:12])([O-:11])=[O:10].[OH-].[Na+]>C(O)C>[Br:1][C:2]1[S:6][C:5]([CH:7]=[CH:12][N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 784285-Bromothiophene-2-carbaldehyde

Product 1

HCID 543993982-Bromo-5-(2-nitro-vinyl)-thiopheneYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using analogous reaction conditions and workup as described in Example 1, step 1, 5-bromo-thiophene-2-carbaldehyde (5 g, 26.17 mmol) in ethanol (100 mL) was reacted with nitro methane (1.4 mL, 26.17 mmol) and 10N NaOH (1.4 mL, 27.47 mmol) to afford 3 g of the product (48.99% yield).

Workup

  1. customreaction conditions and workup

Sources & evidence

ORD record
ord-d1543e3cad964bebae01c01f999ab7af
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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