Cesium carbonate → 2-Isobutyl-5-nitrobenzonitrile

HRID 341328

Reaktionsgleichung

Br[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[CH2:13](B(O)O)[CH:14]([CH3:16])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.O.C(OCC)C>[CH2:13]([C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5])[CH:14]([CH3:16])[CH3:15]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Under an argon gas atmosphere, 2-bromo-5-nitrobenzonitrile (2.0 g), isobutylboronic acid (988 mg), cesium carbonate (5.7 g), and PdCl2 (dppf)-CH2Cl2 (720 mg) were dissolved in toluene (25 ml) and water (1 ml). The mixture was stirred at 100° C. for 18 hours. After the mixture was cooled to room temperature, the mixture was diluted with diethyl ether and water followed by the step of extraction/separation. The organic layer was washed with 1 N-hydrochloric acid, 5 N-sodium hydroxide aqueous solution and saturated brine, and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the resulting residue was purified on column chromatography (EtOAc:hexane=1:3) to obtain the title compound (1.06 g) as a pale yellow oily substance.

Aufarbeitung

temperatureAfter the mixture was cooled to room temperature
customfollowed by the step of extraction/separation
washThe organic layer was washed with 1 N-hydrochloric acid, 5 N-sodium hydroxide aqueous solution and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customAfter the solvent was evaporated under reduced pressure
customthe resulting residue was purified on column chromatography (EtOAc:hexane=1:3)

Quellen und Nachweise

ORD-Eintrag: ord-2103f95a344443ddb9b588fb4cb385b3
Quelldatensatz: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08895753B2

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