Potassium Carbonate → Methyl 2'-methyl-2-nitro-1,1'-biphenyl-4-carboxylate

HRID 219776

Reaktionsgleichung

Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]1([CH3:24])[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.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>[CH3:24][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

To a solution of methyl 4-bromo-3-nitrobenzoate (Chess, 3 g, 11.53 mmol) in toluene (100 mL) and water (100 mL) was added o-tolylboronic acid (1.88 g, 13.84 mmol) followed by potassium carbonate (7.972 g, 57.68 mmol), tetrakis(triphenylphosphine)palladium(0) (0.668 g, 0.577 mmol). The reaction mixture was refluxed at 120° C. for 14 h. After the completion of reaction, it was cooled to RT and organic layer was separated and evaporated under reduced pressure. The crude compound was passed through silica pad (60-120 mesh) using hexane as eluent to give the title compound as a white solid (2.5 g, 79%). 1H NMR: (DMSO-d6, 400 MHz) δ 8.52 (s, 1H), 8.29-8.26 (m, 1H), 7.63-7.61 (m, 1H), 7.34-7.33 (m, 2H), 7.23 (m, 1H), 7.13 (m, 1H), 3.94 (s, 3H), 2.04 (s, 3H).

Aufarbeitung

customAfter the completion of reaction, it
temperaturewas cooled to RT
customorganic layer was separated
customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-41538cc7baf64588a9bc20fb5653d958
Quelldatensatz: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08202865B2

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