Réaction #45805

Équation de réaction

sodium hydrogencarbonate

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

water

→

compound

Rendement 65.0%

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

Rendement 65.0%

Solvants

dichloromethane

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source