Nitromethane → 4-Chloro-2-methoxy-1-(2-nitroethenyl)benzene

HRID 510694Notes

Reaction equation

[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([O:10][CH3:11])[CH:3]=1.[N+:12]([CH3:15])([O-:14])=[O:13].Cl.CN.C([O-])(=O)C.[Na+]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:15]/[N+:12]([O-:14])=[O:13])=[C:4]([O:10][CH3:11])[CH:3]=1

Participants

Reactant 4

HCID 6375Nitromethane

HCID 517045Sodium Acetate

HCID 6364545Methylamine hydrochloride

HCID 138651154-Chloro-2-methoxybenzaldehyde

Product 1

HCID 670805334-Chloro-2-methoxy-1-(2-nitroethenyl)benzeneYield 78.3%

Procedure

4-Chloro-2-methoxybenzaldehyde (250 mg, 1.47 mmol) was diluted with nitromethane (556 μL, 10.3 mmol) followed by the addition of methylamine hydrochloride (59.4 mg, 0.879 mmol) and sodium acetate (72.1 mg, 0.879 mmol). After stirring for 12 hours, the reaction was loaded directly onto a biotage 25 cartridge and eluted with 5% ethyl acetate/hexanes to yield (E)-4-chloro-2-methoxy-1-(2-nitrovinyl)benzene (245 mg, 1.15 mmol, 78.3% yield).

Workup

washeluted with 5% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-1de4ca8dd7a74138848b4826cdf67e5d
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096567B2

Reaction notes

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