反应 #45577

反应方程式

4-Amino-6-bromo-5-methoxy-2-methylbiphenyl-3-carbonitrile

Tribromoborane

sodium carbonate

→

4-Amino-6-bromo-5-hydroxy-2-methylbiphenyl-3-carbonitrile

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
   workup.ADDITIONadded
4. 4
   萃取The organic matter was extracted with ethyl acetate
5. 5
   洗涤washed with saturated brine
6. 6
   干燥dried on anhydrous magnesium sulfate
7. 7
   其他the solvent was evaporated away under reduced pressure
8. 8
   其他to obtain the entitled compound (42.4 mg, quant.) as a pale brown solid

实验过程

4-Amino-6-bromo-5-methoxy-2-methylbiphenyl-3-carbonitrile (I-40) (44.5 mg, 0.14 mmol) was dissolved in dichloromethane (dewatered, 1.4 ml) under nitrogen atmosphere, and cooled in a dry ice-methanol bath at −70° C. 1 M Tribromoborane (dichloromethane solution, 0.42 ml) was dropwise added to it at −70 to −68° C., followed by stirring for 1.5 hours with heating up to 0° C. The reaction liquid was diluted with cold water, and controlled to have a pH of 6 to 7 with aqueous 10% sodium carbonate solution added thereto. The organic matter was extracted with ethyl acetate, washed with saturated brine, then dried on anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure to obtain the entitled compound (42.4 mg, quant.) as a pale brown solid.

来源