Cesium carbonate → Methyl 3-cyano-4-isobutylbenzoate

HRID 1942600Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1942600
[CH3:1][CH:2]([CH3:7])[CH2:3]B(O)O.[C:8]([C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=1OS(C(F)(F)F)(=O)=O)[C:13]([O:15][CH3:16])=[O:14])#[N:9].C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.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].C(Cl)Cl>[C:8]([C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=1[CH2:1][CH:2]([CH3:7])[CH3:3])[C:13]([O:15][CH3:16])=[O:14])#[N:9]

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 2734395(2-Methylpropyl)boronic acidHCID 53821226HCID 53821226, Verbindung

Produkt 1

HCID 59316752Methyl 3-cyano-4-isobutylbenzoateAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of (2-methylpropyl)boronic acid (0.508 g), methyl 3-cyano-4-{[(trifluoromethyl)sulfonyl]oxy}benzoate (D22) (1.4 g) and Cs2CO3 (4.43 g) in toluene (10 mL) and water (1 mL) stirred under nitrogen at room temperature was added PdCl2(dppf)-CH2Cl2 adduct (0.370 g). The reaction mixture was stirred at 100° C. for 12 h. The solvent was removed under reduced pressure. The residue was dissolved in EA (80 mL) and washed with water and brine, dried over anhydrous Na2SO4. The solution was concentrated and the crude product was purified by column chromatography to afford methyl 3-cyano-4-(2-methylpropyl)benzoate (D23) (800 mg) as a colorless oil. MS (ES): C13H15NO2 requires 217. found 218.1 (M+H+).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in EA (80 mL)
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationThe solution was concentrated
  6. customthe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0da8f5b8c84e4484ac2c828c22e458d7
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389508B2

Notizen zur Reaktion

Wird geladen…