Hydrochloric Acid → 1-Bromo-4-cyano-3-methoxy-5-(4-ethyl-benzyl)-benzene

HRID 1359918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1359918
C[C:2]([O-:5])(C)C.[K+].[CH2:7]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](OCC)=O)=[CH:11][CH:10]=1)[CH3:8].[Br:21][C:22]1[CH:27]=C(F)[C:25]([C:29]#[N:30])=[C:24](F)[CH:23]=1.[OH-].[Na+].Cl>CN1C(=O)CCC1.CO>[Br:21][C:22]1[CH:27]=[C:16]([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([CH2:7][CH3:8])=[CH:14][CH:13]=2)[C:25]([C:29]#[N:30])=[C:24]([O:5][CH3:2])[CH:23]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 27569164-Bromo-2,6-difluorobenzonitrileHCID 23665647Potassium tert-butoxideHCID 53419404Ethyl 2-(4-ethylphenyl)acetate

Produkt 1

HCID 583858181-Bromo-4-cyano-3-methoxy-5-(4-ethyl-benzyl)-benzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel2×

Versuchsvorschrift

KOtBu (11.8 g) is added to a flask charged with a stir bar and dry NMP (40 mL) and chilled to −10° C. under argon atmosphere. A solution of ethyl (4-ethyl-phenyl)-acetate (10.1 g) and 1-bromo-4-cyano-3,5-difluoro-benzene (11.5 g) in NMP (40 mL) is added at such a rate that the reaction temperature maintains below 10° C. After stirring for 1 hour at room temperature, methanol (50 mL) and 1 M aqueous sodium hydroxide solution (39 mL) are added and the resulting mixture is stirred overnight at 100° C. Then, 4 M aqueous hydrochloric acid (100 mL) is added and the mixture is stirred for another h at 100° C. The methanol fraction is evaporated, water (200 mL) is added to the residue and the resulting mixture is extracted with ethyl acetate. The combined organic extracts are washed twice with water, twice with brine and dried (MgSO4). The solvent is evaporated and the residue is washed with methanol. The insoluble residue is separated by filtration and dried to give the white product.

Aufarbeitung

  1. additioncharged with a stir bar
  2. custommaintains below 10° C
  3. stirringthe resulting mixture is stirred overnight at 100° C
  4. stirringthe mixture is stirred for another h at 100° C
  5. customThe methanol fraction is evaporated
  6. additionwater (200 mL) is added to the residue
  7. extractionthe resulting mixture is extracted with ethyl acetate
  8. washThe combined organic extracts are washed twice with water, twice with brine
  9. dry with materialdried (MgSO4)
  10. customThe solvent is evaporated
  11. washthe residue is washed with methanol
  12. customThe insoluble residue is separated by filtration
  13. customdried
  14. customto give the white product

Quellen und Nachweise

ORD-Eintrag
ord-e21fe3cf2f8d43e1b161a10802d46379
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879806B2

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