Ammonium Chloride → 3-(4-Bromo-2-methyl-phenyl)-3-cyano-propionic acid methyl ester

HRID 503907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 503907
C([N-]C(C)C)(C)C.[Li+].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]#[N:18])=[C:12]([CH3:19])[CH:11]=1.Br[CH2:21][C:22]([O:24][CH3:25])=[O:23].[NH4+].[Cl-]>C1COCC1.O>[CH3:25][O:24][C:22](=[O:23])[CH2:21][CH:16]([C:13]1[CH:14]=[CH:15][C:10]([Br:9])=[CH:11][C:12]=1[CH3:19])[C:17]#[N:18]

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 60984Methyl bromoacetateHCID 2724682Lithium diisopropylamideHCID 184142962-(4-Bromo-2-methylphenyl)acetonitrile

Produkt 1

HCID 668771313-(4-Bromo-2-methyl-phenyl)-3-cyano-propionic acid methyl esterAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium diisopropylamide (2 M in THF, 110 mL) was added dropwise at −78° C. to a solution of (4-bromo-2-methyl-phenyl)-acetonitrile (38.55 g, 0.1835 mol) in THF (400 mL). The reaction mixture was stirred for 10 minutes and methyl bromoacetate (16.87 mL, 0.1835 mol) was added. The resulting mixture was stirred at −78° C. for 2 hours. A saturated solution of NH4Cl was then added at −78° C. and the resulting mixture was warmed to room temperature. Water was added and the mixture was extracted with EtOAc. The combined organic extracts were washed with water and brine; dried over MgSO4, filtered, and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, 9/1) to give 43.09 g of 3-(4-bromo-2-methyl-phenyl)-3-cyano-propionic acid methyl ester (83% yield) as a yellow oil.

Aufarbeitung

  1. stirringThe resulting mixture was stirred at −78° C. for 2 hours
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified via flash chromatography (hexane/EtOAc, 9/1)

Quellen und Nachweise

ORD-Eintrag
ord-28c08f19384c47e49eed3747fdb5069b
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776910B2

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