تفاعل #45600

معادلة التفاعل

water

dichloromethane

N-(5-cyano-2-fluoro-3-methoxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide

dichloromethane

tribromoborane

→

compound

المردود 88.0%

N-(5-Cyano-2-fluoro-3-hydroxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide

المردود 88.0%

المذيبات

brine

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfterwards, this was heated up to −12° C.
2. 2
   workup.STIRRINGstirred for 30 minutes
3. 3
   أخرىThe reaction liquid
4. 4
   workup.ADDITIONwas added
5. 5
   استخلاصthe intended product was extracted with ethyl acetate (300 ml×2)
6. 6
   تجفيفThe organic layer was dried over anhydrous magnesium sulfate
7. 7
   تركيزconcentrated under reduced pressure
8. 8
   أخرىthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

الإجراء التجريبي

A dichloromethane (60 ml) solution of N-(5-cyano-2-fluoro-3-methoxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide (I-70) (2.02 g, 5.93 mmol) was cooled at −78° C., a dichloromethane solution of 1 N tribromoborane (17.8 ml, 17.8 mmol) was dropwise added, followed by stirring at −78° C. for 15 minutes. Afterwards, this was heated up to −12° C., and stirred for 30 minutes. The reaction liquid was put into cold water (100 ml), saturated brine (50 ml) was added, the intended product was extracted with ethyl acetate (300 ml×2). The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to obtain the entitled compound (1.70 g, 88%) as a yellow solid.

المصدر