Toluene → 3-(1-trityl-1H-imidazol-4-yl)phenol

HRID 1176655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1176655
Br[C:2]1[N:3]=[CH:4][N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.[OH:26][C:27]1[CH:28]=[C:29](OB(O)O)[CH:30]=[CH:31][CH:32]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:7]([N:5]1[CH:6]=[C:2]([C:31]2[CH:32]=[C:27]([OH:26])[CH:28]=[CH:29][CH:30]=2)[N:3]=[CH:4]1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27732744-Bromo-1-trityl-1H-imidazoleHCID 217081833-Hydroxyphenylboric acid

Produkt 1

HCID 684993453-(1-trityl-1H-imidazol-4-yl)phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 0.389 g of 4-bromo-1-trityl-1H-imidazole, 0.152 g of 3-hydroxyphenylboric acid and 10 ml of toluene is admixed with 3 ml of ethanol and 10 ml of aqueous 2N sodium carbonate solution. The mixture is purged with argon for 15 minutes and then 0.026 g of tetrakis(triphenylphosphine)palladium(0) is added. The reaction mixture is stirred at 100° C. for 48 hours, then cooled and poured onto 75 ml of aqueous saturated sodium hydrogencarbonate solution. The mixture is extracted three times with 75 ml of dichloromethane. The combined organic phases are washed with 75 ml of brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a white solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.13 (1:2 EtOAc-heptane); Rt=4.33.

Aufarbeitung

  1. customThe mixture is purged with argon for 15 minutes
  2. addition0.026 g of tetrakis(triphenylphosphine)palladium(0) is added
  3. temperaturecooled
  4. additionpoured onto 75 ml of aqueous saturated sodium hydrogencarbonate solution
  5. extractionThe mixture is extracted three times with 75 ml of dichloromethane
  6. washThe combined organic phases are washed with 75 ml of brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-67c6051362804dabae51467f797412dd
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842688B2

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