Reacción #45805

Ecuación de reacción

sodium hydrogencarbonate

N-(5-Cyano-2-fluoro-4-methoxy-6-methylbiphenyl-3-yl)-2,2-dimethylpropionamide

water

→

compound

Rendimiento 65.0%

N-(5-Cyano-2-fluoro-4-hydroxy-6-methylbiphenyl-3-yl)-2,2-dimethylpropionamide

Rendimiento 65.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGby stirring for 5 minutes
2. 2
   ExtracciónThe solution was extracted twice with dichloromethane
3. 3
   LavadoThe organic layer was washed with saturated brine
4. 4
   Secadodried over anhydrous sodium sulfate
5. 5
   OtroThe insoluble matter was separated by filtration
6. 6
   Otrothe solvent was evaporated away
7. 7
   Otrothe resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=4:1)

Procedimiento

N-(5-Cyano-2-fluoro-4-methoxy-6-methylbiphenyl-3-yl)-2,2-dimethylpropionamide (I-237) (200 mg, 0.59 mmol) was dissolved in dichloromethane (5 ml), and under nitrogen atmosphere at −78° C., 1 M borondichloromethane tribromide solution (1.76 ml, 1.76 mmol) was dropwise added. With stirring, the solution was heated up to 0° C., taking 3 hours. At the same temperature, water with ice was gradually dropwise added to it, followed by stirring for 5 minutes. Further, an aqueous saturated sodium hydrogencarbonate solution was added to the solution to make pH=7. The solution was extracted twice with dichloromethane. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=4:1) to obtain the entitled compound (125 mg, 65%) as a white solid.

Fuente