Ethyl Acetate → 2,3-Difluoro-N-(2-fluoro-4-iodophenyl)-5-methoxy-6-nitroaniline

HRID 240984Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 240984
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[C:14](F)[CH:13]=[C:12]([F:20])[C:11]=1[F:21].C[O-].[Na+].[C:25](OCC)(=[O:27])C>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[C:14]([O:27][CH3:25])[CH:13]=[C:12]([F:20])[C:11]=1[F:21]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 574300722,3,5-trifluoro-N-(2-fluoro-4-iodophenyl)-6-nitroaniline

Produkt 1

HCID 593863122,3-Difluoro-N-(2-fluoro-4-iodophenyl)-5-methoxy-6-nitroanilineAusbeute 47,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred solution of (2-fluoro-4-iodo-phenyl)-(2,3,5-trifluoro-6-nitro-phenyl)-amine (1.23 g, 3 mmol) in dry THF (25 ml) under nitrogen was cooled to −78° C. and a solution of 25% sodium methoxide (0.68 ml, 0.3 mmol) was added slowly. The reaction mixture was allowed to warm to room temperature and stirring continued for another 16 hours. TLC indicated incomplete reaction. Ethyl acetate (100 mL) was added to the reaction mixture and the organic layer was washed with water, dried over sodium sulfate and further purified by column chromatography to provide the desired compound as a yellow solid (0.6 g, 47.6%). m/z=424 [M+H]+.

Aufarbeitung

  1. customreaction
  2. washthe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. customfurther purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4ca59364f5384164adcf00cb0acae9fe
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648116B2

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