Dichloromethane → (2'-Formyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

HRID 38703

Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=1.Br[C:24]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][C:25]=1[CH:26]=[O:27].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>COCCOC.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.O>[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1[CH:6]=[C:7]([C:24]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][C:25]=2[CH:26]=[O:27])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

[4-Methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester (4.99 g, 16.4 mmol), 2-bromo-5-trifluoromethyl-benzaldehyde (4.15 g, 16.4 mmol), and potassium carbonate (5.67 g, 41.0 mmol) were combined in DME (40 mL) and H2O (20 mL), and the mixture was purged with N2 for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (1.90 g, 1.64 mmol) was added, and the reaction was stirred at 90° C. for 10 hours. The mixture was worked-up with CH2Cl2 and H2O, and the organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography to give the title compound.

Aufarbeitung

customH2O (20 mL), and the mixture was purged with N2 for 30 minutes
dry with materialthe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag: ord-798993da5a854441b8f77ec2812121f9
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08524748B2

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