Реакция #45577

Уравнение реакции

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

Tribromoborane

sodium carbonate

→

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

Растворители

dichloromethane

water

Условия реакции

Обработка

1. 1
   Температураwith heating up to 0° C
2. 2
   ДругоеThe reaction liquid
3. 3
   workup.ADDITIONadded
4. 4
   ЭкстракцияThe organic matter was extracted with ethyl acetate
5. 5
   Промывкаwashed with saturated brine
6. 6
   Сушкаdried on anhydrous magnesium sulfate
7. 7
   Другоеthe solvent was evaporated away under reduced pressure
8. 8
   Другоеto obtain the entitled compound (42.4 mg, quant.) as a pale brown solid

Методика

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.

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