Potassium Carbonate → Methyl 4-amino-2'-bromo-2-biphenylcarboxylate

HRID 269564

Reaktionsgleichung

[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.[NH2:11][C:12]1[CH:13]=[CH:14][C:15](Br)=[C:16]([CH:21]=1)[C:17]([O:19][CH3:20])=[O:18].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>[NH2:11][C:12]1[CH:21]=[C:16]([C:17]([O:19][CH3:20])=[O:18])[C:15]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])=[CH:14][CH:13]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

A mixture of 2-bromophenyl boronic acid (600 mg, 3.0 mmol), methyl 5-amino-2-bromobenzoate (1.5 g, 6.5 mmol), potassium carbonate (2.07 g, 15 mmol) and tetrakis(triphenylphosphine)palladium (0) (345 mg, 5 mol %) in 1:1 toluene/ethanol (20 ml) was stirred and heated at 90° C. under nitrogen for 12 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 dichloromethane/iso-hexane (1:2->1:1) to yield the title compound as a pale yellow gum. (682 mg, 74%).

Aufarbeitung

temperatureAfter cooling the mixture
dry with materialthe organic phase dried (MgSO4)
customevaporated to dryness
customThe residue was chromatographed with dichloromethane/iso-hexane (1:2->1:1)

Quellen und Nachweise

ORD-Eintrag: ord-273f753770b94019aec781ec869b4b74
Quelldatensatz: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07446222B2

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