تفاعل #45641

معادلة التفاعل

tetrahydrofuran

tetrahydrofuran

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

sodium hydrogencarbonate

→

compound

المردود 70.0%

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

المردود 70.0%

المذيبات

Ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling
2. 2
   أخرىthe reaction liquid
3. 3
   تركيزwas concentrated under reduced pressure
4. 4
   أخرىazeotroped with benzene
5. 5
   غسيلby washing with water and saturated brine
6. 6
   تركيزThe 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
    درجة الحرارةAfter cooling
11. 11
    أخرىthe reaction liquid
12. 12
    تركيزwas concentrated under reduced pressure
13. 13
    workup.ADDITIONdiluted with ethyl acetate
14. 14
    غسيلwashed with saturated brine
15. 15
    تركيزThe organic layer was concentrated under reduced pressure

الإجراء التجريبي

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.

المصدر