N-methyl-2-pyrrolidone → 2-Nitrobiphenyl-4-carbonitrile

HRID 1893550Notes

Reaction equation

CN1CCCC1=O.Cl[C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18].[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[F-].[Cs+]>C(OCC)(=O)C.O.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+:17]([C:10]1[CH:11]=[C:12]([C:13]#[N:14])[CH:15]=[CH:16][C:9]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([O-:19])=[O:18]

Participants

Conditions

Temperature: 100 °C

Procedure

To N-methylpyrrolidone (25 ml) were added 4-chloro-3-nitrobenzonitrile (1.79 g, 9.80 mmol), phenylboronic acid (1.53 g, 12.5 mmol), cesium fluoride (3.90 g, 25.7 mmol) and bis(triphenylphosphine)palladium(II) dichloride (447 mg, 0.637 mmol), and the mixture was stirred with heating at 100° C. for 9 hr. The reaction mixture was cooled, diluted with ethyl acetate and water, and the insoluble material was filtered off through celite. The organic layer was extracted 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 (1.74 g, yield 79%) as a yellow solid.

Workup

temperatureThe reaction mixture was cooled
filtrationthe insoluble material was filtered off through celite
extractionThe organic layer was extracted
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-b0f8eb1906bd483a81e2270e40acacdb
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513235B2

Reaction notes

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