反应 #45553

反应方程式

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

tribromoborane

sodium carbonate

→

compound

收率 82.5%

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

收率 82.5%

溶剂

dichloromethane

water

反应条件

后处理

1. 1
   温度with heating up to 0° C
2. 2
   其他The reaction liquid
3. 3
   萃取The organic matter was extracted with ethyl acetate
4. 4
   洗涤washed with saturated brine
5. 5
   干燥dried on anhydrous magnesium sulfate
6. 6
   其他the solvent was evaporated away under reduced pressure
7. 7
   其他The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→3:2)

实验过程

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.

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