تفاعل #45553

معادلة التفاعل

N-(2-Bromo-5-cyano-3-methoxy-6-methyl-3′-nitrobiphenyl-4-yl)-2,2-dimethylpropionamide

tribromoborane

sodium carbonate

→

compound

المردود 82.5%

N-(2-Bromo-5-cyano-3-hydroxy-6-methyl-3′-nitrobiphenyl-4-yl)-2,2-dimethylpropionamide

المردود 82.5%

المذيبات

dichloromethane

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwith heating up to 0° C
2. 2
   أخرىThe reaction liquid
3. 3
   استخلاصThe organic matter was extracted with ethyl acetate
4. 4
   غسيلwashed with saturated brine
5. 5
   تجفيفdried on anhydrous magnesium sulfate
6. 6
   أخرىthe solvent was evaporated away under reduced pressure
7. 7
   أخرىThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→3:2)

الإجراء التجريبي

N-(2-Bromo-5-cyano-3-methoxy-6-methyl-3′-nitrobiphenyl-4-yl)-2,2-dimethylpropionamide (I-12) (630 mg, 1.41 mmol) was dissolved in dichloromethane (dewatered, 20 ml) under nitrogen atmosphere, cooled at −70° C. in a dry ice-methanol bath. 1 M tribromoborane (dichloromethane solution) (4.23 ml) was dropwise added to it at −70° C. to −68° C., followed by stirring for 2 hours with heating up to 0° C. The reaction liquid was diluted with cold water, followed by pH control at 6 to 7 by addition of aqueous 10% sodium carbonate solution. The organic matter was extracted with ethyl acetate, washed with saturated brine, dried on anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→3:2) to obtain the entitled compound (503 mg, 82%) as a pale yellow solid.

المصدر