Sodium Iodide → 6-bromo-8-ethoxy-4H-benzo[1,3]dioxine

HRID 2079153

Reaktionsgleichung

Reaktionsgleichung von HRID 2079153
FC(F)(F)[C:3]([OH:5])=[O:4].C(C1C=CC(N[CH:18]([C:34]2[CH:39]=[C:38]([O:40][CH3:41])[C:37](OC)=C[C:35]=2F)C2NC(=O)N(C3C=CC=CC=3C(O)=O)N=2)=CC=1)(=N)N.[H-].[Na+].[Br:47][CH2:48]Cl.[I-].[Na+].[Cl-].[NH4+].[CH3:54]N(C=O)C>C(OCC)(=O)C>[Br:47][C:48]1[CH:37]=[C:38]([O:40][CH2:41][CH3:54])[C:39]2[O:5][CH2:3][O:4][CH2:18][C:34]=2[CH:35]=1

Komponenten

8

Edukt 6

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 6333BromochloromethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1363370832-{3-[(4-carbamimidoylphenylamino)-(2-fluoro-4,5-dimethoxyphenyl)methyl]5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}benzoic Acid Trifluoroacetate

Produkt 1

HCID 670968006-bromo-8-ethoxy-4H-benzo[1,3]dioxine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of this compound in 40 ml of DMF there was added 1g of sodium hydride (60% oily suspension) while cooling on ice, and the mixture was stirred at room temperature for 30 minutes. After then adding 1 ml of bromochloromethane and 0.25 g of sodium iodide to the reaction mixture, it was stirred at 80° C. for 6 hours under a hydrogen atmosphere. Saturated aqueous ammonium chloride was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give 6-bromo-8-ethoxy-4H-benzo[1,3]dioxine (1.62 g).

Aufarbeitung

  1. temperaturewhile cooling on ice
  2. stirringwas stirred at 80° C. for 6 hours under a hydrogen atmosphere
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationThe desiccating agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Quellen und Nachweise

ORD-Eintrag
ord-035d2348da454e09b4cd0f7fbaefe427
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928228B2

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