Nitromethane → (E)-2-methoxy-1-(2-nitrovinyl)-4-(trifluoromethyl)benzene

HRID 1021353Notes

Reaction equation

HRID 1021353 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[N+:15]([CH3:18])([O-:17])=[O:16].Cl.CN.C([O-])(=O)C.[Na+]>>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:4]=1/[CH:5]=[CH:18]/[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 4

HCID 6375NitromethaneHCID 517045Sodium AcetateHCID 49847042-Methoxy-4-(trifluoromethyl)benzaldehydeHCID 6364545Methylamine hydrochloride

Product 1

HCID 67080220(E)-2-methoxy-1-(2-nitrovinyl)-4-(trifluoromethyl)benzeneYield 65.6%

Procedure

A portion of 2-methoxy-4-(trifluoromethyl)benzaldehyde (3.78 g, 18.5 mmol) was diluted with nitromethane (7.02 ml, 130 mmol) followed by the addition of methylamine hydrochloride (0.750 g, 11.1 mmol) and sodium acetate (0.911 g, 11.1 mmol). After stirring for 12 hours, the reaction was loaded directly onto a biotage 40 cartridge and eluted with 5% ethyl acetate/hexanes to 20% ethyl acetate hexanes to yield (E)-2-methoxy-1-(2-nitrovinyl)-4-(trifluoromethyl)benzene (3.0 g, 12.1 mmol, 65.6% yield).

Workup

  1. washeluted with 5% ethyl acetate/hexanes to 20% ethyl acetate hexanes

Sources & evidence

ORD record
ord-518414dddf9f4f91bdd6e74dbe7e421b
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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