Reaction #45575

Reaction equation

potassium carbonate

N-(2-bromo-5-cyano-3-methoxy-6-methylbiphenyl-4-yl)2,2,2-trifluoroacetamide

→

compound

Yield 94.0%

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

Yield 94.0%

Solvents

methanol

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Othermethanol was evaporated away under reduced pressure
3. 3
   Extractionfollowed by extraction with ethyl acetate
4. 4
   Washwashing with saturated brine
5. 5
   Dryingdrying on anhydrous magnesium sulfate
6. 6
   Concentrationthe solvent was concentrated under reduced pressure
7. 7
   Otherto obtain a pale brown residue
8. 8
   OtherThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1)

Procedure

Aqueous potassium carbonate solution (1.25 ml) [potassium carbonate (15 g) was dissolved in water (100 ml)] and methanol (1.25 ml) were added to N-(2-bromo-5-cyano-3-methoxy-6-methylbiphenyl-4-yl)2,2,2-trifluoroacetamide (I-38) (133 mg, 0.322 mmol), followed by stirring overnight at 70° C. After cooling, methanol was evaporated away under reduced pressure, followed by extraction with ethyl acetate, washing with saturated brine and drying on anhydrous magnesium sulfate, the solvent was concentrated under reduced pressure to obtain a pale brown residue. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1) to obtain the entitled compound (95 mg, 94%) as a colorless solid.

Source