2-Fluoroaniline → 3-chloro-N-(2-fluorophenyl)propanamide

HRID 1521670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521670
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[Cl:9][CH2:10][CH2:11][C:12](Cl)=[O:13]>O1CCCC1.N1C=CC=CC=1.O>[Cl:9][CH2:10][CH2:11][C:12]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[F:1])=[O:13]

Komponenten

6

Edukt 2

HCID 95842-FluoroanilineHCID 693643-Chloropropionyl chloride

Produkt 1

HCID 42560293-chloro-N-(2-fluorophenyl)propanamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 2-fluoroaniline (20.00 g, 180.0 mmol) in tetrahydrofurane (100 mL) and pyridine (22 mL) was stirred for 15 min, and then 3-chloropropionyl chloride (25.14 g, 198 mmol) in tetrahydrofurane (50 ml) was added at 0° C. The mixture was stirred for 18 h at room temperature under inert atmosphere. After completion of the reaction, the mixture was diluted with water. The aqueous layer was separated and extracted with diethylether. The collected organic parts were washed with water and brine, then dried over Na2SO4, filtered and concentrated under vacuum to afford the title compound (white solid). This intermediate was used directly in the next step without further purification and characterization.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customThe aqueous layer was separated
  3. extractionextracted with diethylether
  4. washThe collected organic parts were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c7b1e0deeb154d20bd775617967711c0
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073929B2

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