Fluorobenzene → HCID 10610346, Verbindung

HRID 1382200Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1382200
[C:1]([C:5]1[C:10]([C:11]([OH:13])=O)=[CH:9][N:8]=[CH:7][CH:6]=1)([O:3]C)=[O:2].[Al+3].[Cl-].[Cl-].[Cl-].[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O=S(Cl)Cl>[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:11]([C:10]2[CH:9]=[N:8][CH:7]=[CH:6][C:5]=2[C:1]([OH:3])=[O:2])=[O:13])=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 10008FluorobenzeneHCID 3275254-(Methoxycarbonyl)pyridine-3-carboxylic acidHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 10610346HCID 10610346, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

A mixture of 4-carbomethoxynicotinic acid (2.0 g, 11.04 mmol) in 20 mL of SOCl2 is heated to reflux for 4 hours, then allowed to cool. Evaporation of excess SOCl2 results in 4-carbomethoxynicotinoyl chloride HCl which is suspended in fluorobenzene (15 ml) and treated with AlCl3 (4.04 g, 30.3 mmol). After heating at reflux for 2 hours, the reaction is quenched with ice and neutralized with aqueous NaOH to generate a precipitate which is filtered. The aqueous fraction of the biphasic filtrate is separated, washed with several portions of EtOAc and acidified to pH 3.5 with 5% aqueous HCl to generate a white solid. The solid is collected by filtration, washed with H2O, and dried by suction to generate 3-(4-fluorobenzoyl)pyridine-4-carboxylic acid.

Aufarbeitung

  1. temperatureis heated
  2. temperatureto reflux for 4 hours
  3. temperatureto cool
  4. customEvaporation of excess SOCl2
  5. customresults in 4-carbomethoxynicotinoyl chloride HCl which
  6. temperatureAfter heating
  7. temperatureat reflux for 2 hours
  8. customthe reaction is quenched with ice and neutralized with aqueous NaOH
  9. filtrationis filtered
  10. customThe aqueous fraction of the biphasic filtrate is separated
  11. washwashed with several portions of EtOAc
  12. filtrationThe solid is collected by filtration
  13. washwashed with H2O
  14. customdried by suction

Quellen und Nachweise

ORD-Eintrag
ord-b12e931f38b5493f93ad0b0cb277e512
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04806535

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