Ethanol → 2-Benzyloxy-[1,1';2',1'']terphenyl-3''-carboxylic acid ethyl ester

HRID 269537

Reaktionsgleichung

Reaktionsgleichung von HRID 269537
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2Br)[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2].[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O)C.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:12]2[C:13]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[O:26][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 2773253(2-(Benzyloxy)phenyl)boronic acidHCID 587309812'-Bromobiphenyl-3-carboxylic acid ethyl ester

Produkt 1

HCID 587309952-Benzyloxy-[1,1';2',1'']terphenyl-3''-carboxylic acid ethyl esterAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2′-Bromobiphenyl-3-carboxylic acid ethyl ester (153 mg, 0.5 mmol) and 2-benzyloxyphenylboronic acid (125 mg (0.55 mmol) were dissolved in 1:1 toluene:ethanol (5 ml) under nitrogen. Potassium carbonate (552 mg, 4 mmol) and tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol) were added and the mixture heated at 90° C. for 3 h. After cooling, the solvent was evaporated. The residue was partitioned between diethyl ether and water and the organic phase washed with water, dried (MgSO4) and the solvent removed in vacuo. The residue was flash chromatographed (silica gel, 2-10% EtOAc-isohexane) to give the title compound as a clear oil (84 mg, 41%). LC/MS Rt=4.09 [(M−OEt)H+]=363.1.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe solvent was evaporated
  3. customThe residue was partitioned between diethyl ether and water
  4. washthe organic phase washed with water
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customchromatographed (silica gel, 2-10% EtOAc-isohexane)

Quellen und Nachweise

ORD-Eintrag
ord-3b5e8a42ac9e4fa988a54bd09ce21266
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446222B2

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