Ammonium Chloride → 2-Chloro-5-(2,3-difluorobenzoyl)pyridine

HRID 277930

Reaktionsgleichung

Reaktionsgleichung von HRID 277930
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[F:9].C([Li])CCC.[Cl:15][C:16]1[CH:27]=[CH:26][C:19]([C:20](N(OC)C)=[O:21])=[CH:18][N:17]=1.[NH4+].[Cl-]>C1COCC1>[Cl:15][C:16]1[CH:27]=[CH:26][C:19]([C:20](=[O:21])[C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=2[F:9])=[CH:18][N:17]=1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 27332601-Bromo-2,3-difluorobenzeneHCID 114355976-Chloro-N-methoxy-N-methylnicotinamideHCID 178418339Butyllithium

Produkt 1

HCID 226266622-Chloro-5-(2,3-difluorobenzoyl)pyridineAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 1-bromo-2,3-difluorobenzene (0.114 g, 0.746 mmol) in 3 ml of dry THF was added, at −78° C., n-butyl lithium (1.6 M in hexane, 0.47 ml, 0.749 mmol). The reaction mixture was stirred at this temperature for 1 hour. A solution of 6-chloro-N-methoxy-N-methyl-nicotinamide (0.13 g, 0.68 mmol) in 5 ml of THF was added and the reaction mixture was allowed to warm to RT and stir for 6 hours. Saturated NH4Cl was added and the mixture was extracted with CH2Cl2 (3×10 ml). The organic layers were combined, washed with brine, and dried over NaSO4. The solvents were removed in vacuo and the residue was purified by column chromatography (Hex/AcOEt 9:1) to give 130 mg (77%) of an oily product. IR, NMR.

Aufarbeitung

  1. stirringstir for 6 hours
  2. extractionthe mixture was extracted with CH2Cl2 (3×10 ml)
  3. washwashed with brine
  4. dry with materialdried over NaSO4
  5. customThe solvents were removed in vacuo
  6. customthe residue was purified by column chromatography (Hex/AcOEt 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-cb0eaa22d06545359b18611473bc8c02
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06358971B1

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