Hydrochloric Acid → 3-(2',4'-Difluoro-4-biphenylyl)-2-butenoic acid ethyl ester

HRID 26941

Reaktionsgleichung

Reaktionsgleichung von HRID 26941
NC1C=CC(C2C=CC(F)=CC=2F)=CC=1.Cl.N([O-])=O.[Na+].[Li+].[Cl-].C(OC(=O)/C=C/C)C.[CH2:31]([O:33][C:34](=[O:53])[C:35](Cl)=[C:36]([C:38]1[CH:43]=[CH:42][C:41]([C:44]2[CH:49]=[CH:48][C:47]([F:50])=[CH:46][C:45]=2[F:51])=[CH:40][CH:39]=1)[CH3:37])[CH3:32]>[Zn].C(O)(=O)C.CC(C)=O.O>[CH2:31]([O:33][C:34](=[O:53])[CH:35]=[C:36]([C:38]1[CH:43]=[CH:42][C:41]([C:44]2[CH:49]=[CH:48][C:47]([F:50])=[CH:46][C:45]=2[F:51])=[CH:40][CH:39]=1)[CH3:37])[CH3:32]

Komponenten

11

Edukt 6

HCID 313Hydrochloric AcidHCID 429065Ethyl trans-crotonateHCID 433294Lithium ChlorideHCID 27582662',4'-Difluoro-[1,1'-biphenyl]-4-amineHCID 23668193Sodium NitriteHCID 537897532-Chloro-3-(2',4'-difluoro-4-biphenylyl)-2-butenoic acid ethyl ester

Produkt 1

HCID 541080583-(2',4'-Difluoro-4-biphenylyl)-2-butenoic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel2×HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

20.5 g. of 4-amino-2',4'-difluorobiphenyl are dissolved in a mixture of 25 ml. of 35% hydrochloric acid, 50 ml. of acetic acid and 120 ml. of water. The solution is cooled to 0° and 6.9 g. of NaNO2 are added in portions. Subsequently, a solution of 1.5 g. of Cu2Cl2, 0.9 g. of LiCl and 100 g. of crotonic acid ethyl ester in 900 ml. of acetone is added drop-wise at -10° to the stirred mixture under a N2 atmosphere. The mixture is stirred for 4 hours more at 0°-5° and for 14 hours at 20° and extracted with benzene. The extract is washed and evaporated to give 20 g. of crude 2-chloro-3-(2',4'-difluoro-4-biphenylyl)-2-butenoic acid ethyl ester. This is dissolved in 250 ml. of acetic acid to which 50 g. of zinc dust are added. The mixture is stirred for 3 hours at 20° and filtered. After the customary work up, 3-(2',4'-difluoro-4-biphenylyl)-2-butenoic acid ethyl ester, m.p. 54°-56°, is obtained from the filtrate.

Aufarbeitung

  1. temperatureThe solution is cooled to 0°
  2. extractionextracted with benzene
  3. washThe extract is washed
  4. customevaporated
  5. customto give 20 g
  6. dissolutionThis is dissolved in 250 ml
  7. stirringThe mixture is stirred for 3 hours at 20°
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-a770b524ce354360884f65f0ca48658c
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04151302

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