Dimethylformamide → Benzonitrile, 4-ethenyl-3-nitro-

HRID 1893548Notes

Reaction equation

CN(C)C=O.Cl[C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[N+:15]([O-:17])=[O:16].[CH2:18](C([Sn])=C(CCCC)CCCC)[CH2:19]CC>C(OCC)(=O)C.CCCCCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N+:15]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:7]=1[CH:18]=[CH2:19])[C:11]#[N:12])([O-:17])=[O:16]

Participants

Conditions

Temperature: 100 °C

Procedure

To N,N-dimethylformamide (50 ml) were added 4-chloro-3-nitrobenzonitrile (2.81 g, 15.39 mmol), tri-n-butylvinyltin (5.23 g, 16.49 mmol) and bis(triphenylphosphine)palladium(II) dichloride (701 mg, 0.999 mmol), and the mixture was stirred with heating at 100° C. for 160 min. The reaction mixture was cooled, diluted with an ethyl acetate-hexane=1:1 mixed solvent, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (2.21 g, yield 82%) as a yellow solid.

Workup

temperatureThe reaction mixture was cooled
washwashed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationThe insoluble material was filtered off
concentrationthe solution was concentrated under reduced pressure
customThe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record: ord-5f0b3110899b44b584f113a00c6e350b
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513235B2

Reaction notes

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