Potassium Phosphate, Tribasic → Methyl 4'-(2-ethoxyethoxy)-6-methoxy-2',6'-dimethylbiphenyl-3-carboxylate

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Reaktionsgleichung

Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].[CH2:14]([O:16][CH2:17][CH2:18][O:19][C:20]1[CH:25]=[C:24]([CH3:26])[C:23](B(O)O)=[C:22]([CH3:30])[CH:21]=1)[CH3:15].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH2:14]([O:16][CH2:17][CH2:18][O:19][C:20]1[CH:21]=[C:22]([CH3:30])[C:23]([C:2]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=2)=[C:24]([CH3:26])[CH:25]=1)[CH3:15]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

A mixture of methyl 3-bromo-4-methoxybenzoate (0.90 g, 3.67 mmol), [4-(2-ethoxyethoxy)-2,6-dimethylphenyl]boronic acid (0.87 g, 3.67 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.13 g, 0.15 mmol), 2-(dicyclohexylphosphino)biphenyl (79 mg, 0.22 mmol), tripotassium phosphate (1.56 g, 7.34 mmol) and toluene (20 mL) was stirred under a nitrogen atmosphere at 90° C. for 18 hr. After cooling the reaction mixture, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=1/1) to give the title compound (0.71 g, yield 54%) as a yellow oil.

Aufarbeitung

temperatureAfter cooling the reaction mixture
filtrationthe insoluble material was filtered off
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=1/1)

Quellen und Nachweise

ORD-Eintrag: ord-fd9db33895e24109b900871e42fb4b64
Quelldatensatz: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07786165B2

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