Potassium Carbonate → HCID 22057729, Verbindung

HRID 1828710Notizen

Reaktionsgleichung

Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10][CH3:11].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].[NH4+].[Cl-]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:10]([C:3]1[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[CH:9][C:2]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:11]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

A mixture of 4-bromo-3-ethyl benzonitrile (1 g, 4.76 mmol), phenylboronic acid (1.16 g, 9.5 mmol), K2CO3 (1.97 g, 14.3 mmol), and Pd(PPh3)4 (543 mg, 0.48 mmol) in DMF (anhydrous, 15 mL) is heated in a sealed tube at 120° C. for 12 h. After cooling to room temperature, the reaction mixture is poured into a mixture of ice and saturated aqueous NH4Cl. The mixture is extracted with EtOAc (3×30 mL). The combined organic layers are washed with saturated aqueous NaCl, dried over Na2SO4, and concentrated. The crude product obtained is purified by silica gel chromatography (5% EtOAc in hexanes) to give 2-ethyl-biphenyl-4-carbonitrile as a colorless oil.

Aufarbeitung

temperatureAfter cooling to room temperature
extractionThe mixture is extracted with EtOAc (3×30 mL)
washThe combined organic layers are washed with saturated aqueous NaCl
dry with materialdried over Na2SO4
concentrationconcentrated
customThe crude product obtained
customis purified by silica gel chromatography (5% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-ffd18a6920074f0c918ea703a843d42d
Quelldatensatz: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07060697B2

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