Pyridine → N-(4-bromo-2-fluorophenyl)acetamide

HRID 400596

Reaktionsgleichung

Reaktionsgleichung von HRID 400596
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([F:9])[CH:3]=1.N1C=CC=CC=1.[C:16](Cl)(=[O:18])[CH3:17]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:16](=[O:18])[CH3:17])=[C:4]([F:9])[CH:3]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 1230504-Bromo-2-fluoroaniline

Produkt 1

HCID 67593N-(4-bromo-2-fluorophenyl)acetamideAusbeute 96,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-bromo-2-fluorophenylamine (10.9 g, 57.4 mmol) and pyridine (9.4 mL, 115 mmol) in 50 mL of anhydrous dichloromethane was treated with acetyl chloride (3.33 mL, 63.1 mmol) at 0° C. After 10 minutes at 0° C. and 10 minutes at room temperature, the mixture was concentrated in vacuo and the residue was treated with 300 mL of 1 N aqueous sulfuric acid. The organic layer was concentrated in vacuo to give 12.9 g of N-(4-bromo-2-fluorophenyl)acetamide as a light greyish solid (97% yield).

Aufarbeitung

  1. concentration10 minutes at room temperature, the mixture was concentrated in vacuo
  2. additionthe residue was treated with 300 mL of 1 N aqueous sulfuric acid
  3. concentrationThe organic layer was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5484457b9215413597298fc2147dafa2
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741897B2

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