Sodium Carbonate → 3'-Methyl-biphenyl-3-carboxylic acid ethyl ester

HRID 719704

Reaktionsgleichung

Reaktionsgleichung von HRID 719704
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15](C)=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2].Br[C:20]1C=C(C=CC=1)C(OCC)=O.CC1C=C(B(O)O)C=CC=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([CH3:20])[CH:17]=2)[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Komponenten

9

Edukt 5

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 90488Ethyl 3-bromobenzoateHCID 27339503-Tolylboronic acidHCID 107287544'-Methyl-biphenyl-3-carboxylic acid ethyl ester

Produkt 1

HCID 586105893'-Methyl-biphenyl-3-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3′-Methyl-biphenyl-3-carboxylic acid ethyl ester was synthesized as described for 4′-methyl-biphenyl-3-carboxylic acid ethyl ester. Ethyl 3-bromobenzoate (3.83 g, 16.72 mmol, 1 eq.) and 3-methylbenzeneboronic acid (2.5 g, 18.39 mmol, 1.1 eq.) in THF were treated with aqueous sodium carbonate (2M solution, 18.4 mL, 36.78 mmol, 2.2 eq.), palladium(II) acetate (0.37 g, 1.67 mmol, 10 mol %), triphenylphosphine (1.93 g, 7.35 mmol, 4.4×Pd), and copper(I) iodide (0.1 g, catalyst). When complete, the reaction was worked up as described leaving a brown oil.

Aufarbeitung

  1. customas described leaving a brown oil

Quellen und Nachweise

ORD-Eintrag
ord-e65df2a6181a4dff925d97d874621ff9
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132456B2

Verknüpfte Notizen

Wird geladen…