Sodium Hydroxide → 1-Bromo-4-cyano-3-(4-methoxy-benzyl)-benzene

HRID 19832

Reaktionsgleichung

Reaktionsgleichung von HRID 19832
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](OCC)=O)=[CH:5][CH:4]=1.[Br:15][C:16]1[CH:21]=C[C:19]([C:22]#[N:23])=[C:18](F)[CH:17]=1.CC(C)([O-])C.[K+].[OH-].[Na+]>CN1CCCC1=O.CO>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]#[N:23])=[C:10]([CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH:21]=1

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 84174Ethyl 4-methoxyphenylacetateHCID 7360294-Bromo-2-fluorobenzonitrileHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 593463491-Bromo-4-cyano-3-(4-methoxy-benzyl)-benzene

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

A mixture of 25 g of ethyl (4-methoxy-phenyl)-acetate, 27.4 g of 1-bromo-4-cyano-3-fluoro-benzene and 20 mL of N-methyl-pyrrolidin-2-one is slowly added to 31.4 g of potassium tert butoxide in 130 mL of N-methyl-pyrrolidin-2-one keeping the temperature below 10° C. After stirring for 1 hour at room temperature, 100 mL of methanol and 137 mL of 1 M aqueous sodium hydroxide are added and the mixture is stirred overnight at room temperature. The methanol fraction is evaporated, the residue is basified with 1 M aqueous sodium hydroxide and extracted with tert butyl-methyl ether. The aqueous phase is acidified with 4 M hydrochloric acid and extracted with ethyl acetate several times. The combined ethyl acetate extracts are evaporated and the residue together with 120 mL of N,N-dimethyl formamide and 24.9 g of potassium carbonate heated at 100° C. for 1 hour. The reaction mixture is diluted with aqueous sodium bicarbonate and extracted several times with ethyl acetate. The combined extracts are evaporated and the residue crystallized from methanol.

Aufarbeitung

  1. stirringthe mixture is stirred overnight at room temperature
  2. customThe methanol fraction is evaporated
  3. extractionextracted with tert butyl-methyl ether
  4. extractionextracted with ethyl acetate several times
  5. customThe combined ethyl acetate extracts are evaporated
  6. temperaturethe residue together with 120 mL of N,N-dimethyl formamide and 24.9 g of potassium carbonate heated at 100° C. for 1 hour
  7. additionThe reaction mixture is diluted with aqueous sodium bicarbonate
  8. extractionextracted several times with ethyl acetate
  9. customThe combined extracts are evaporated
  10. customthe residue crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-912e420520564572abf02fde032e2b08
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745414B2

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