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

HRID 510691Notes

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

Reactant 4

HCID 6375Nitromethane

HCID 517045Sodium Acetate

HCID 6364545Methylamine hydrochloride

HCID 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

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

Sources & evidence

ORD record: ord-a979b9bb90b346308b0fb688937ce298
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096567B2

Reaction notes

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