Potassium Phosphate, Tribasic → HCID 68459588, Verbindung

HRID 502450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502450
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=[C:6]([O:18][CH3:19])[CH:5]=1.[CH:21]1(B(O)O)[CH2:23][CH2:22]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>CC([O-])=O.CC([O-])=O.[Pd+2].O.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:5]=[C:6]([O:18][CH3:19])[CH:7]=[C:8]([CH:21]2[CH2:23][CH2:22]2)[CH:9]=1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 54576351HCID 54576351, Verbindung

Produkt 1

HCID 68459588HCID 68459588, VerbindungAusbeute 96,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

The above prepared 3-methoxy-5-trifluoromethanesulfonyloxy-benzoic acid methyl ester (0.350 g, 1.11 mmol) was dissolved under Ar in 4.5 ml of abs. toluene and 0.49 ml of water and treated successively with cyclopropyl boronic acid (0.191 g, 2 eq.), K3PO4 (1.272 g, 5.4 eq.), tricyclohexylphosphine (0.069 g, 0.22 eq.), and finally Pd(OAc)2 (0.028 g, 0.11 eq.). The reaction flask was closed with a septum and the mixture was allowed to react for 16 h at 100° C. Pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (silica gel, hexane/AcOEt=9/1), afforded 0.221 g of the title compound as yellow oil, 97% pure according to GC-analysis.

Aufarbeitung

  1. dissolutionwas dissolved under Ar in 4.5 ml of abs
  2. customThe reaction flask was closed with a septum
  3. customto react for 16 h at 100° C
  4. additionPouring
  5. extractionice/NH4Cl, twofold extraction with AcOEt
  6. washwashing with water
  7. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Quellen und Nachweise

ORD-Eintrag
ord-dd7fd60ce4eb4572949635ddbf83f9d6
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772253B2

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