Triphenylphosphine → 2'-Acetyl[1,1'-biphenyl]-4-carbonitrile

HRID 270621

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O)(=[O:22])[CH3:21].O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl[C:42]1[CH:49]=[CH:48][C:45]([C:46]#[N:47])=[CH:44][CH:43]=1>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.C1(C)C=CC=CC=1>[C:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:42]1[CH:49]=[CH:48][C:45]([C:46]#[N:47])=[CH:44][CH:43]=1)(=[O:22])[CH3:21]

Participants

Conditions

Temperature: 80 °C

Procedure

Bis(triphenylphosphine)palladium dichloride (PdCl2(PPh3)2) (0.6 g, 0.86 mmol), triphenylphosphine (0.44 g, 1.74 mmol), (2-acetylphenyl)boronic acid (6 g, 3.76 mmol) and tripotassium phosphate hydrate (16 g, 7.54 mmol) were placed in a flask. Nitrogen was blown into the flask and then the flask was filled with toluene (40 ml) and 4-chlorbenzonitrile (4 g, 2.90 mmol). The reaction mixture was stirred at 80° C. for 4 hours. The reaction mixture was cooled and washed with water. The organic layer was dried over sodium sulfate and then the solvent was evaporated. The product, 2′-acetyl-4-biphenylcarbonitrile (5a) was purified by a column (hexane/ethyl acetate=8/1). Yield: 3.3 g (51%).

Workup

temperatureThe reaction mixture was cooled
washwashed with water
dry with materialThe organic layer was dried over sodium sulfate
customthe solvent was evaporated
customThe product, 2′-acetyl-4-biphenylcarbonitrile (5a) was purified by a column (hexane/ethyl acetate=8/1)

Sources & evidence

ORD record: ord-6a8ed67d0e5942ddaf4af41eeb0a8c3e
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449574B2

Linked notes

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