N-(4-chloro-2,5-dimethoxyphenyl)-3-fluoro-4-methoxybenzamide → N-(4-Chloro-2,5-dihydroxyphenyl)-3-fluoro-4-hydroxybenzamide

HRID 858225

Reaktionsgleichung

Reaktionsgleichung von HRID 858225
[Cl:1][C:2]1[C:7]([O:8]C)=[CH:6][C:5]([NH:10][C:11](=[O:21])[C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[C:14]([F:20])[CH:13]=2)=[C:4]([O:22]C)[CH:3]=1>C(Cl)Cl>[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([NH:10][C:11](=[O:21])[C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([F:20])[CH:13]=2)=[C:4]([OH:22])[CH:3]=1

Komponenten

3

Edukt 1

HCID 8409357N-(4-chloro-2,5-dimethoxyphenyl)-3-fluoro-4-methoxybenzamide

Produkt 1

HCID 21907381N-(4-Chloro-2,5-dihydroxyphenyl)-3-fluoro-4-hydroxybenzamideAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Boron trifluoride dimethyl sulfide complex (70 mL) was added into a mixture of N-(4-chloro-2,5-dimethoxyphenyl)-3-fluoro-4-methoxybenzamide (1.75 g, 5.15 mmol) and CH2Cl2 (35 mL). After stirring for 20 h, the solvent and the excess reagent were evaporated under a nitrogen stream in the hood. The residue was taken in a mixture of ice and HCl (1N) and extracted with EtOAc. The organic layer was washed with HCl (1N) and dried over MgSO4. Evaporation and purification by flash chromatography (CH2Cl2/hexanes/EtOAc 5/3/2, and AcOH 10 mL per 1 liter of the eluting solvent) gave a white solid (1.4 g, 91% yield, m.p. 254–256° C.); MS m/e 296 (M−H)+.

Aufarbeitung

  1. customthe solvent and the excess reagent were evaporated under a nitrogen stream in the hood
  2. additionThe residue was taken in a mixture of ice and HCl (1N)
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with HCl (1N)
  5. dry with materialdried over MgSO4
  6. customEvaporation and purification by flash chromatography (CH2Cl2/hexanes/EtOAc 5/3/2, and AcOH 10 mL per 1 liter of the eluting solvent)

Quellen und Nachweise

ORD-Eintrag
ord-5acb907bd7bd40eda99a857aaab1ed4e
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148247B2

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