تفاعل #80923

معادلة التفاعل

2-amino-5-bromo-6-methylbenzonitrile

sodium carbonate

toluene

3-fluoro-5-trifluoromethylphenylboronic acid

→

2-amino-6-methyl-5-(3-fluoro-5-trifluoromethylphenyl)benzonitrile

المردود 103.0%

المذيبات

water

ethanol

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONUpon completion of addition
2. 2
   استخلاصThe mixture was then extracted with four 100 mL portions of ethyl acetate
3. 3
   تجفيفThe combined extracts were dried with magnesium sulfate
4. 4
   ترشيحfiltered
5. 5
   تركيزThe filtrate was concentrated under reduced pressure to a residue
6. 6
   غسيلElution
7. 7
   تركيزconcentrated under reduced pressure

الإجراء التجريبي

Under a dry nitrogen atmosphere, 0.5 gram (0.0004 mole) of tetrakis(triphenylphosphine)palladium(0) was added to a stirred mixture of 2.8 grams (0.0132 mole) of 2-amino-5-bromo-6-methylbenzonitrile (prepared as in Step C of Example 1), 35 mL of aqueous 2M sodium carbonate and 50 mL of toluene. To this was then added dropwise a solution of 3.3 grams (0.0159 mole) of 3-fluoro-5-trifluoromethylphenylboronic acid in 10 mL of ethanol. Upon completion of addition, the reaction mixture was warmed to about 80° C., where it was stirred for seven hours. After this time the reaction mixture was poured into 200 mL of water. The mixture was then extracted with four 100 mL portions of ethyl acetate. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished with methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 4.0 grams of 2-amino-6-methyl-5-(3-fluoro-5-trifluoromethylphenyl)benzonitrile, mp 96°-97° C. The NMR spectrum was consistent with the proposed structure.

المصدر