Реакция #45553

Уравнение реакции

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

tribromoborane

sodium carbonate

→

compound

Выход 82.5%

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

Выход 82.5%

Растворители

dichloromethane

water

Условия реакции

Обработка

1. 1
   Температураwith heating up to 0° C
2. 2
   ДругоеThe reaction liquid
3. 3
   ЭкстракцияThe organic matter was extracted with ethyl acetate
4. 4
   Промывкаwashed with saturated brine
5. 5
   Сушкаdried on anhydrous magnesium sulfate
6. 6
   Другоеthe solvent was evaporated away under reduced pressure
7. 7
   ДругоеThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→3:2)

Методика

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.

Источник