Sodium Carbonate → Ethyl 2'-methyl[1,1'-biphenyl]-3-carboxylate

HRID 719723

Reaktionsgleichung

Reaktionsgleichung von HRID 719723
[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.C1(C)C=CC=CC=1B(O)O.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]=[CH:16][C:17]=2[CH3:20])[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Komponenten

9

Edukt 5

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 90488Ethyl 3-bromobenzoateHCID 27332672-Methylphenyl boronic acidHCID 107287544'-Methyl-biphenyl-3-carboxylic acid ethyl ester

Produkt 1

HCID 12853045Ethyl 2'-methyl[1,1'-biphenyl]-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Versuchsvorschrift

2′-Methyl-biphenyl-3-carboxylic acid ethyl ester was synthesized as described for 4′-methyl-biphenyl-3-carboxylic acid ethyl ester. Ethyl 3-bromobenzoate (8.02 g, 35.03 mmol, 1 eq.) and o-tolylboronic acid (5.0 g, 36.78 mmol, 1.05 eq.) in THF were treated with aqueous 2M sodium carbonate (38.5 mL, 77.07 mmol, 2.2 eq.), palladium(II) acetate (0.79 g, 3.50 mmol, 10 mol %), triphenylphosphine (4.04 g, 15.40 mmol, 4.4×Pd), and copper(I) iodide (0.22 g, catalyst). When complete, the reaction was worked up as described leaving a dark brown oil.

Aufarbeitung

  1. customas described leaving a dark brown oil

Quellen und Nachweise

ORD-Eintrag
ord-bd5da445a8064ef199454b371e0862a1
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132456B2

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