Ethanol → Ethyl 2-chloro-4-fluoro-5-nitrobenzoate

HRID 48486Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 48486
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH2:19](O)[CH3:20].C(N(CC)CC)C>C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([O:6][CH2:19][CH3:20])=[O:5]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 72108282-Chloro-4-fluoro-5-nitrobenzoic Acid

Produkt 1

HCID 22508453Ethyl 2-chloro-4-fluoro-5-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

First, 50 g (0.29 mol) of 2-chloro-4-fluorobenzoic acid was dissolved in 150 ml of hydrochloric acid at room temperature, to which a mixed acid of 28 ml (0.31 mol) of fuming nitric acid and 56 ml of concentrated sulfuric acid was added dropwise at 35° to 45° C. Then, the solution was stirred at 40° C. for 1 hour and poured into 250 ml of ice-water. The precipitated crystals were collected by filtration and recrystallized from a mixed solution of hexane and ethyl acetate, which afforded 55 g (0.25 mol) of 2-chloro-4-fluoro-5-nitrobenzoic acid. Then, 55 g (0.25 mol) of 2-chloro-4-fluoro-5-nitrobenzoic acid was dissolved in 50 ml of ethyl acetate, to which 33 g (0.28 mol) of thionyl chloride was added, and the mixture was heated under reflux for 3 hours and then allowed to stand for cooling to room temperature. Then, 20 ml of ethanol and 30 g of triethylamine were added under ice cooling, and the mixture was stirred at room temperature for 2 hours. The solvent was distilled out, and the residue was purified by silica gel chromatography, which afforded 57 g (0.23 mol) of ethyl 2-chloro-4-fluoro-5-nitrobenzoate.

Aufarbeitung

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. distillationThe solvent was distilled out
  5. customthe residue was purified by silica gel chromatography, which

Quellen und Nachweise

ORD-Eintrag
ord-ec0140a251b0413f87e0b245af03ffaf
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703503B2

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