N-(4-fluorophenyl)acetamide → HCID 59437302, Verbindung

HRID 244467

Reaktionsgleichung

Reaktionsgleichung von HRID 244467
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[CH:6][CH:5]=1.[Br:14][C:15]1[CH:20]=[CH:19][C:18](F)=[C:17]([N+:22]([O-:24])=[O:23])[CH:16]=1>C1COCC1>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([N:10]([C:7]2[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=2)[C:11](=[O:13])[CH3:12])=[C:17]([N+:22]([O-:24])=[O:23])[CH:16]=1

Komponenten

5

Edukt 3

HCID 9601N-(4-fluorophenyl)acetamideHCID 24758Sodium hydrideHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Produkt 1

HCID 59437302HCID 59437302, VerbindungAusbeute 39,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a room temperature suspension of sodium hydride (33.4 mmol, 1.34 g of 60% in mineral oil) in 60 mL of THF was added a solution of the N-(4-fluorophenyl)acetamide (4.1 g, 26.8 mmol) in THF (30 mL) over a 5 minute period. After 30 minutes, a solution of 4-bromo-1-fluoro-2-nitrobenzene (3.2 mL, 26.8 mmol) in THF (10 mL) was added. After 15 hours, the reaction was concentrated in vacuo, the residue was diluted with 1 N sulfuric acid (300 mL) and extracted with three 100 mL portions of methylene chloride. The combined organic layers were washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to afford a brownish oil. The residue was purified by column chromatography over silica gel eluting with 0-100% ethyl acetate in hexanes to afford 3.7 g of N-(4-bromo-2-nitrophenyl)-N-(4-fluorophenyl)acetamide as a thick yellow oil. MS m/z 353/355 (MH+).

Aufarbeitung

  1. waitAfter 15 hours
  2. concentrationthe reaction was concentrated in vacuo
  3. additionthe residue was diluted with 1 N sulfuric acid (300 mL)
  4. extractionextracted with three 100 mL portions of methylene chloride
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto afford a brownish oil
  9. customThe residue was purified by column chromatography over silica gel eluting with 0-100% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-5835df7ae1a34871b3b3f4832d9ce855
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658637B2

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