Nitromethane → 1,2-difluoro-4-[(E)-2-nitroethenyl]benzene

HRID 1843953Notes

Reaction equation

HRID 1843953 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.[N+:11]([CH3:14])([O-:13])=[O:12].[OH-].[Na+]>C(O)C>[F:10][C:9]1[CH:8]=[CH:7][C:4](/[CH:5]=[CH:14]/[N+:11]([O-:13])=[O:12])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 5880883,4-Difluorobenzaldehyde

Product 1

HCID 247212971,2-difluoro-4-[(E)-2-nitroethenyl]benzeneYield 76.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using analogous reaction conditions and workup as described in example 1, 3,4-difluorobenzaldehyde (5 g, 35.1864 mmol) in ethanol (175 mL) was reacted math nitro methane (1.9 mL, 35.1864 mmol) and 10N NaOH (1.47 g, 36.9457 mmol) to afford 5 g of the product (76.80% yield). 1H NMR (CDCl3, 300 MHz): δ 7.92 (d, 1H), 7.58-7.0 (m, 4H).

Workup

  1. customreaction conditions and workup

Sources & evidence

ORD record
ord-1152dfde708845e3a80500b8c507098b
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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