Reaktion #45553

Reaktionsgleichung

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

tribromoborane

sodium carbonate

→

compound

Ausbeute 82.5%

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

Ausbeute 82.5%

Lösungsmittel

dichloromethane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwith heating up to 0° C
2. 2
   SonstigeThe reaction liquid
3. 3
   ExtraktionThe organic matter was extracted with ethyl acetate
4. 4
   Waschenwashed with saturated brine
5. 5
   Trocknendried on anhydrous magnesium sulfate
6. 6
   Sonstigethe solvent was evaporated away under reduced pressure
7. 7
   SonstigeThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→3:2)

Vorschrift

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.

Quelle