Reaktion #45641

Reaktionsgleichung

tetrahydrofuran

tetrahydrofuran

2-amino-5-bromo-4-fluoro-3-hydroxy-6-methylbenzonitrile

sodium hydrogencarbonate

→

compound

Ausbeute 70.0%

N-(4-Bromo-2-cyano-5-fluoro-6-hydroxy-3-methylphenyl)-2,2-dimethyl-3-[(phenylmethyl)oxy]propionamide

Ausbeute 70.0%

Lösungsmittel

Ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Sonstigethe reaction liquid
3. 3
   Einengenwas concentrated under reduced pressure
4. 4
   Sonstigeazeotroped with benzene
5. 5
   Waschenby washing with water and saturated brine
6. 6
   EinengenThe organic layer was concentrated under reduced pressure
7. 7
   workup.DISSOLUTIONthe resulting residue was dissolved in ethanol (30 ml)
8. 8
   workup.ADDITIONaqueous 1 N sodium hydroxide solution (24 ml) was added
9. 9
   workup.STIRRINGby stirring at 50° C. for 23 hours
10. 10
    TemperaturAfter cooling
11. 11
    Sonstigethe reaction liquid
12. 12
    Einengenwas concentrated under reduced pressure
13. 13
    workup.ADDITIONdiluted with ethyl acetate
14. 14
    Waschenwashed with saturated brine
15. 15
    EinengenThe organic layer was concentrated under reduced pressure

Vorschrift

After cooling, the reaction liquid was concentrated under reduced pressure, and azeotroped with benzene. A tetrahydrofuran solution (7 ml) of the resulting residue was dropwise added to a tetrahydrofuran solution (63 ml) of 2-amino-5-bromo-4-fluoro-3-hydroxy-6-methylbenzonitrile (I-75) (3.13 g, 12.77 mmol) and sodium hydrogencarbonate (2.68 g, 31.93 mmol), followed by stirring at room temperature for 19 hours. Ethyl acetate was added to the reaction liquid, followed by washing with water and saturated brine. The organic layer was concentrated under reduced pressure, the resulting residue was dissolved in ethanol (30 ml), aqueous 1 N sodium hydroxide solution (24 ml) was added, followed by stirring at 50° C. for 23 hours. After cooling, the reaction liquid was concentrated under reduced pressure, diluted with ethyl acetate, neutralized with aqueous 1 N hydrochloric acid, washed with saturated brine. The organic layer was concentrated under reduced pressure to obtain the entitled compound (5.82 g, 70%) as a yellow white solid.

Quelle