Potassium Phosphate, Tribasic → Methyl 2,6-dimethoxybiphenyl-4-carboxylate

HRID 1096976Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1096976
Br[C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:14][CH3:15].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].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].CC#N>[CH3:15][O:14][C:3]1[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[C:11]([O:12][CH3:13])[C:2]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 117713Methyl 4-bromo-3,5-dimethoxybenzoate

Produkt 1

HCID 57930909Methyl 2,6-dimethoxybiphenyl-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

PdCl2(dppf) (14.8 g) was added to a CH3CN (900 mL) solution of methyl 4-bromo-3,5-dimethoxybenzoate (25.0 g), phenylboronic acid (22.2 g), Bu4NBr (5.86 g) and K3PO4 (77.2 g), and stirred under heat for 14 hours. This was filtered through Celite, and the filtrate was concentrated and purified through column chromatography to obtain the title compound as a colorless solid.

Aufarbeitung

  1. temperatureunder heat for 14 hours
  2. filtrationThis was filtered through Celite
  3. concentrationthe filtrate was concentrated
  4. custompurified through column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d3f5b8e3929b4e0d9c1c794ccf02fcd9
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138197B2

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