Potassium Carbonate → Benzoic acid, 5-amino-2-chloro-4-methyl-, methyl ester

HRID 2065736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2065736
[CH3:1][O:2][C:3](=[O:13])[C:4]1[C:9](Br)=[C:8]([NH2:11])[CH:7]=[CH:6][C:5]=1[Cl:12].[C:14](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([NH2:11])[C:7]([CH3:14])=[CH:6][C:5]=1[Cl:12]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 68606931HCID 68606931, Verbindung

Produkt 1

HCID 57423009Benzoic acid, 5-amino-2-chloro-4-methyl-, methyl esterAusbeute 71,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 5-amino-6-bromo-2-chloro-benzoic acid methyl ester (0.5 g, 1.89 mmol) in dioxane (10 ml) and water (1 ml) was added potassium carbonate (0.784 g, 5.67 mmol), PdCl2(dppf) (0.54 g, 0.189 mmol) and trimethyl boroxine (0.276 ml, 1.985 mmol). The mixture was stirred at 110° C. for 18 hours, then cooled to room temperature and filtered. The filtrate was concentrated to dryness under reduced pressure. Purification of the residue by flash chromatography (hexanes:EtOAc 8:2) gave 0.270 g (71%) of 5-amino-2-chloro-4-methyl-benzoic acid methyl ester as a tan solid.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated to dryness under reduced pressure
  4. customPurification of the residue by flash chromatography (hexanes:EtOAc 8:2)

Quellen und Nachweise

ORD-Eintrag
ord-d6d07fa856a2452187d218b821a7811b
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288552B2

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