Potassium Carbonate → Ethyl 4-(acetylamino)-2'-bromo-2-biphenylcarboxylate

HRID 269576

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

A mixture of 2-bromophenylboronic acid (1.61 g, 8.0 mmol), ethyl 5-(acetylamino)-2-bromobenzoate (2.15 g, 7.5 mmol), potassium carbonate (5.52 g, 40 mmol) and tetrakis(triphenylphosphine)palladium(0) (869 mg, 0.75 mmol) in 1:1 toluene/ethanol (40 ml) was stirred and heated at 90° C. under nitrogen for 2 hours. After cooling the mixture was diluted with diethyl ether and water and the organic phase dried (MgSO4) and evaporated to dryness. The residue was chromatographed with ethyl acetate/iso-hexane (2:3) to yield 1.33 g of the title compound as a white foam.

Aufarbeitung

temperatureAfter cooling the mixture
dry with materialthe organic phase dried (MgSO4)
customevaporated to dryness
customThe residue was chromatographed with ethyl acetate/iso-hexane (2:3)

Quellen und Nachweise

ORD-Eintrag: ord-1892fcaeedce4a5c819686acab73fe16
Quelldatensatz: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07446222B2

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