4-Fluorobiphenyl → HCID 15541120, Verbindung

HRID 381819

Reaktionsgleichung

Reaktionsgleichung von HRID 381819
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[C:18]([CH2:22][CH2:23][C:24](Cl)=[O:25])([O:20][CH3:21])=[O:19]>ClCCl>[F:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:24](=[O:25])[CH2:23][CH2:22][C:18]([O:20][CH3:21])=[O:19])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 94614-FluorobiphenylHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 15541120HCID 15541120, VerbindungAusbeute 74,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a stirred suspension of anhydrous aluminum chloride (9.64 g, 0.723 mol) in dichloromethane (90 mL) at 5° C. was added dropwise a solution of 4-fluorobiphenyl (4.97 g, 0.0289 mol) in dichloromethane (40 mL) followed by the dropwise addition of a solution of 3-carbomethoxypropionyl chloride (3.94 mL, 0.032 mol) in dichloromethane (30 mL), and the mixture stirred. After 2 hours at 5° C., the mixture was allowed to warm to room temperature. After 1 day, the reaction was cooled to 5° C. and quenched by the dropwise addition of water (160 mL). The layers were separated, and the organic layer washed with brine, dried (Na2SO4), and rotary evaporated. The residue was recrystallized from methanol (300 mL) to give 6.17 g of 4-(4′-fluoro-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester as a pale yellow solid; mp 131.5-133.0° C.

Aufarbeitung

  1. waitAfter 1 day
  2. temperaturethe reaction was cooled to 5° C.
  3. customquenched by the dropwise addition of water (160 mL)
  4. customThe layers were separated
  5. washthe organic layer washed with brine
  6. dry with materialdried (Na2SO4), and rotary evaporated
  7. customThe residue was recrystallized from methanol (300 mL)

Quellen und Nachweise

ORD-Eintrag
ord-e554754d25da4b91b1ad3a91d61b2761
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06307089B2

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