Stannous Chloride → 5-bromo-1-(4-fluorophenyl)-2-methyl-1H-benzimidazole

HRID 244468

Reaktionsgleichung

Reaktionsgleichung von HRID 244468
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:9](=O)[CH3:10])=[C:4]([N+:19]([O-])=O)[CH:3]=1.[Sn](Cl)Cl>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[C:9]([CH3:10])=[N:19][C:4]=2[CH:3]=1

Komponenten

4

Edukt 2

HCID 24479Stannous ChlorideHCID 59437302N-(4-bromo-2-nitrophenyl)-N-(4-fluorophenyl)acetamide

Produkt 1

HCID 594373055-bromo-1-(4-fluorophenyl)-2-methyl-1H-benzimidazoleAusbeute 25,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred room temperature solution of N-(4-bromo-2-nitrophenyl)-N-(4-fluorophenyl)acetamide (3.7 g, 10.8 mmol) in ethanol (75 mL) was added tin (II) chloride (6 g, 31.4 mmol) and the mixture was warmed at 90° C. After 3 hours, the mixture was cooled, concentrated in vacuo, diluted with cold water, made basic with 2 N NaOH (pH 11), and extracted with three 75 mL portions of methylene chloride. The combined organic layers were washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to afford a reddish brown oil. The residue was purified by column chromatography over silica gel eluting with 0-50% ethyl acetate in methylene chloride to afford 830 mg of 5-bromo-1-(4-fluorophenyl)-2-methyl-1H-benzimidazole as an off-white solid.

Aufarbeitung

  1. temperaturethe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. additiondiluted with cold water
  4. extractionextracted with three 75 mL portions of methylene chloride
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto afford a reddish brown oil
  9. customThe residue was purified by column chromatography over silica gel eluting with 0-50% ethyl acetate in methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-269ac4b146d64aeabcef2f6db67097bf
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658637B2

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