Benzoic acid, 4-fluoro-, ethyl ester → 2-(4-Chloropyridin-2-yl)-1-(4-fluorophenyl)ethan-1-one

HRID 1062863

Reaktionsgleichung

Reaktionsgleichung von HRID 1062863
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.[F:9][C:10]1[CH:20]=[CH:19][C:13]([C:14](OCC)=[O:15])=[CH:12][CH:11]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:14]([C:13]2[CH:19]=[CH:20][C:10]([F:9])=[CH:11][CH:12]=2)=[O:15])[CH:3]=1

Komponenten

5

Edukt 3

HCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 5813924-Chloro-2-methylpyridineHCID 2733832Lithium Hexamethyldisilazide

Produkt 1

HCID 218740612-(4-Chloropyridin-2-yl)-1-(4-fluorophenyl)ethan-1-oneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a cold (0° C.) solution of 4-chloro-2-picoline (5.0 g, 39 mmol) and ethyl 4-fluorobenzoate (6.6 g, 39 mmol) in tetrahydrofuran (100 mL) was added lithium bis(trimethylsilyl)amide (80 mL, 1.0 M in tetrahydrofuran, 80 mmol) dropwise via a pressure equalizing funnel over 30 minutes. Upon complete addition, the cold bath was removed and the resulting solution was stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure and methanol was added to the reaction, resulting in the formation of a white precipitate. The precipitate was collected by filtration and dried to give 2-(4-chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone (9.6 g, 99%) as a white solid. 1H NMR (DMSO-d6): δ 7.90 (m, 3H), 7.11 (t, 2H), 6.56 (s, 1H), 5.67 (s, 1H), 4.14 (m, 2H); 19F NMR (DMSO-d6): δ−115.67; MS m/z 250 (M+1).

Aufarbeitung

  1. customover 30 minutes
  2. additionUpon complete addition
  3. customthe cold bath was removed
  4. concentrationThe reaction mixture was concentrated under reduced pressure and methanol
  5. additionwas added to the reaction
  6. customresulting in the formation of a white precipitate
  7. filtrationThe precipitate was collected by filtration
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7777abee73d44836bf098056adec1866
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06962914B2

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