Reaktion #2166396

Reaktionsgleichung

bromochloromethane

4-bromo-2-(2-hydroxyethyl)-6-methoxyphenol

1g

2-{3-[(4-carbamimidoylphenylamino)-(2-fluoro-4,5-dimethoxyphenyl)methyl]5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}benzoic Acid trifluoroacetate

sodium bistrimethylsilylamide

ammonium chloride

→

title compound

2-bromo-4-methoxy-8,9-dihydro-5,7-dioxabenzocycloheptene

Lösungsmittel

ethyl acetate

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile cooling on ice
2. 2
   workup.STIRRINGwas stirred at 80° C. for 20 hours under a nitrogen atmosphere
3. 3
   TrocknenThe organic layer was dried over anhydrous magnesium sulfate
4. 4
   FiltrationThe desiccating agent was filtered off
5. 5
   Einengenthe filtrate was concentrated under reduced pressure
6. 6
   SonstigeThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Vorschrift

To a solution of 898 mg of 4-bromo-2-(2-hydroxyethyl)-6-methoxyphenol in 10 ml of DMF there was added 1g of sodium bistrimethylsilylamide while cooling on ice, and the mixture was stirred at room temperature for 30 minutes. After adding 1 ml of bromochloromethane to the reaction mixture, it was stirred at 80° C. for 20 hours under a nitrogen 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 the title compound (420 mg) as an oil.

Quelle