Nitromethane → 2-chloro-1-[(E)-2-nitroethenyl]-4-(trifluoromethyl)benzene

HRID 1048086Notes

Reaction equation

HRID 1048086 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[N+:14]([CH3:17])([O-:16])=[O:15].Cl.CN.C([O-])(=O)C.[Na+]>>[Cl:1][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1/[CH:4]=[CH:17]/[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 4

HCID 6375NitromethaneHCID 517045Sodium AcetateHCID 6364545Methylamine hydrochlorideHCID 130761442-Chloro-4-(trifluoromethyl)benzaldehyde

Product 1

HCID 57031342-chloro-1-[(E)-2-nitroethenyl]-4-(trifluoromethyl)benzeneYield 33.2%

Procedure

2-chloro-4-(trifluoromethyl)benzaldehyde (400 mg, 1.92 mmol) was diluted with nitromethane (727 μl, 13.4 mmol) followed by the addition of methylamine hydrochloride (77.7 mg, 1.15 mmol) and sodium acetate (94.4 mg, 1.15 mmol). After stirring for 12 hours, the reaction was loaded directly onto a biotage 25 cartridge and eluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to yield (E)-2-chloro-1-(2-nitrovinyl)-4-(trifluoromethyl)benzene (160 mg, 0.636 mmol, 33.2% yield).

Workup

  1. washeluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-ee84620c05a34a658eb2f6b7f6808379
Source dataset
uspto-grants-2013_10
Patent number
US08569522B2

Reaction notes

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