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

HRID 921966Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 921966
[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 the 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 and were then dried over Na2SO4, filtered and concentrated under vacuum to afford the title compound as a white solid. This intermediate was used directly in the next step without further purification and characterization.

Aufarbeitung

  1. customAfter the 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 materialwere then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-69c6041e9f6c445e88670bdd375e20a8
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278093B2

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