Hydrochloric Acid → Ethyl (2-fluoro-4-nitrophenyl)acetate

HRID 2240216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2240216
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH:11]([C:16]([O:18][CH3:19])=[O:17])C(OC)=O.O.[Cl-].[Li+].[Cl-].[Na+].Cl.[CH3:26]S(C)=O>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][C:16]([O:18][CH2:19][CH3:26])=[O:17]

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 962WaterHCID 5234Sodium ChlorideHCID 433294Lithium ChlorideHCID 53429620Dimethyl 2-(2-fluoro-4-nitrophenyl)malonate

Produkt 1

HCID 56776686Ethyl (2-fluoro-4-nitrophenyl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

500 mg (1.84 mmol) of dimethyl (2-fluoro-4-nitrophenyl)malonate are dissolved in 10 ml of DMSO. 33.2 mg (1.84 mmol) of water and 313 mg (7.37 mmol) of lithium chloride are added, and the mixture is heated at 100° C. for 3 hours. The reaction solution is then poured into 30 ml of ethyl acetate and shaken with saturated sodium chloride solution and with dilute hydrochloric acid. The mixture is dried over sodium sulfate and the solvent is removed under reduced pressure. The oil obtained is purified by preparative HPLC. The product fractions are extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is removed under reduced pressure. This gives an oil which, after seeding with product crystals, quickly crystallizes.

Aufarbeitung

  1. dry with materialThe mixture is dried over sodium sulfate
  2. customthe solvent is removed under reduced pressure
  3. customThe oil obtained
  4. customis purified by preparative HPLC
  5. extractionThe product fractions are extracted with ethyl acetate
  6. dry with materialThe combined organic phases are dried over sodium sulfate
  7. customthe solvent is removed under reduced pressure
  8. customThis gives an oil which
  9. customquickly crystallizes

Quellen und Nachweise

ORD-Eintrag
ord-9e0ec4a134a94e80b6b2110756aabd4d
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723347B2

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