Sodium Carbonate → HCID 53840489, Verbindung

HRID 1267106Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1267106
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1OS(C(F)(F)F)(=O)=O.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+].[F:29][C:30]([F:41])([F:40])[C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1>C1(C)C=CC=CC=1.CCO.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>[CH3:1][O:2][C:3]([C:4]1[C:5]([C:34]2[CH:35]=[CH:36][C:31]([C:30]([F:41])([F:40])[F:29])=[CH:32][CH:33]=2)=[CH:6][C:7]([O:10][CH3:11])=[CH:8][CH:9]=1)=[O:20]

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 10710352Methyl 4-methoxy-2-(trifluoromethylsulfonyloxy)benzoate

Produkt 1

HCID 53840489HCID 53840489, VerbindungAusbeute 91,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-methoxy-2-(trifluoro-methanesulfonyloxy)-benzoic acid methyl ester (6.28 g) in toluene (100 mL) was added LiCl (2.54 g) and Pd(PPh3)4 (1.15 g). After few minutes at room temperature, a 2M solution of Na2CO3 (26 mL) was added followed by a solution of 4-trifluoromethylphenyl boronic acid (4.17 g) in EtOH (30 mL). The resulting mixture was stirred under reflux for 6 hours. The mixture was cooled to room temperature and the phases were separated. The organic layer was then dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography eluting with hexane/AcOEt (90/10) to give the title compound (5.7 g) as white crystals.

Aufarbeitung

  1. waitAfter few minutes at room temperature
  2. temperatureunder reflux for 6 hours
  3. customthe phases were separated
  4. dry with materialThe organic layer was then dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography
  8. washeluting with hexane/AcOEt (90/10)

Quellen und Nachweise

ORD-Eintrag
ord-41dd6f3e84d0416aa32fd6f77b72f4ba
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06552022B1

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