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22568-07-6

22568-07-6 Structure

22568-07-6 Structure
IdentificationBack Directory
[Name]

1-chloro-2-[(E)-2-nitroethenyl]benzene
[CAS]

22568-07-6
[Synonyms]

1-chloro-2-[(e)-2-nitrovinyl]benzene
1-chloro-2-[(E)-2-nitroethenyl]benzene
Benzene, 1-chloro-2-[(1E)-2-nitroethenyl]-
Benzene, 1-chloro-2-(2-nitroethenyl)-, (E)-
(E)-1-chloro-2-(2-nitrovinyl)benzene(WXC07116)
[Molecular Formula]

C8H6ClNO2
[MOL File]

22568-07-6.mol
[Molecular Weight]

183.59
Chemical PropertiesBack Directory
[storage temp. ]

2-8°C
Hazard InformationBack Directory
[Synthesis]

Nitromethane

75-52-5

2-Chlorobenzaldehyde

89-98-5

1-chloro-2-[(E)-2-nitroethenyl]benzene

22568-07-6

GENERAL METHOD: Hexylamine (20 mg, 0.2 mmol) was added to a solution of toluene (4 mL) containing 3a (212 mg, 2.0 mmol), silica gel (200 mg) and nitromethane (134 mg, 2.2 mmol). The reaction mixture was stirred at 90 °C for 4 hours. After completion of the reaction, the silica gel was removed by filtration and the filter cake was washed with toluene. The filtrate was concentrated under reduced pressure at 40 °C to give the crude product. The crude product was purified by silica gel column chromatography using heptane-acetone (5:1, v/v) as eluent to afford the target compound 5a (268 mg, 90% yield).

[References]

[1] Tetrahedron Letters, 2018, vol. 59, # 4, p. 392 - 396
[2] Patent: CN105566276, 2016, A. Location in patent: Paragraph 0469; 0470; 0471
[3] Patent: US2014/45872, 2014, A1. Location in patent: Paragraph 0331
[4] Journal of the American Chemical Society, 1934, vol. 56, p. 1556,1558
[5] Journal of the Chemical Society, 1940, p. 446,447
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