Potassium Carbonate → 2-Benzyloxy-4''chloro-[1,1';2',1'']terphenyl-2''-carboxylic acid ethyl ester

HRID 269536

Reaktionsgleichung

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[C:16](B(O)O)=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:25]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:26]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28].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>[CH2:30]([O:29][C:27]([C:26]1[C:25]([C:16]2[C:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:35][CH:34]=[C:33]([Cl:36])[CH:32]=1)=[O:28])[CH3:31]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

A mixture of 2′-benzyloxy-biphenyl-2-boronic acid (61 mg, 0.2 mmol), ethyl 2-bromo-5-chlorobenzoate (53 mg, 0.2 mmol), potassium carbonate (207 mg, 1.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (23 mg, 0.02 mmol) in 1:1 toluene/ethanol (3 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 purified using Biotage with ethyl acetate/iso-hexane (1:19) to yield the title compound as a colourless gum (63 mg, 71%).

Aufarbeitung

temperatureAfter cooling the mixture
dry with materialthe organic phase dried (MgSO4)
customevaporated to dryness
customThe residue was purified

Quellen und Nachweise

ORD-Eintrag: ord-554492d8a9e24c0aa3c8dadbf2bc3aba
Quelldatensatz: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07446222B2

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