Water → 4-tert-Butyl 4'-methyl 2,6-diethoxybiphenyl-4,4'-dicarboxylate

HRID 38482

Reaktionsgleichung

O.[CH3:2][O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9](B(O)O)=[CH:8][CH:7]=1)=[O:5].Br[C:16]1[C:28]([O:29][CH2:30][CH3:31])=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:18][C:17]=1[O:32][CH2:33][CH3:34].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:33]([O:32][C:17]1[CH:18]=[C:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:27]=[C:28]([O:29][CH2:30][CH3:31])[C:16]=1[C:9]1[CH:10]=[CH:11][C:6]([C:4]([O:3][CH3:2])=[O:5])=[CH:7][CH:8]=1)[CH3:34]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

H2O (261 mg, 14.48 mmol) was added to a stirred mixture of PdCl2(dppf) (106 mg, 0.145 mmol), [4-(methoxycarbonyl)phenyl]boronic acid (626 mg, 3.48 mmol), tert-butyl 4-bromo-3,5-diethoxybenzoate (1.00 g, 2.90 mmol) and K3PO4 (1.23 g, 5.79 mmol) in DME (8 ml) and the mixture was stirred at 100° C. overnight. The reaction mixture was filtered through celite pad, the filtrate was concentrated under reduced pressure. The residue was purified by silicage column chromatography (hexane/EtOAc) to give intended compound as a colorless solid.

Aufarbeitung

filtrationThe reaction mixture was filtered through celite pad
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silicage column chromatography (hexane/EtOAc)
customto give

Quellen und Nachweise

ORD-Eintrag: ord-b276a56e587f4d9d87a49145d9afba45
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08524730B2

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