تفاعل #45308

معادلة التفاعل

ethyl acetate hexane

4-amino-3-iodobenzotrifluoride

copper cyanide

→

2-amino-5-(trifluoromethyl)benzonitrile

المردود 105.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىIn a 2-liter flask equipped with a septum inlet, magnetic stirring bar, and condenser
2. 2
   درجة الحرارةThe contents were cooled to 40° C.
3. 3
   ترشيحfiltered through a pad of Celite
4. 4
   غسيلThe solids were washed with ether
5. 5
   أخرىthe filtrate transferred to a separatory funnel
6. 6
   غسيلwashed with about 5% aqueous ammonium hydroxide
7. 7
   استخلاصThe aqueous layer was back-extracted with ether
8. 8
   غسيلwashed with brine
9. 9
   تجفيفdried over magnesium sulfate
10. 10
    ترشيحfiltered
11. 11
    تركيزconcentrated
12. 12
    أخرىto yield a black oil
13. 13
    أخرىThe oil was chromatographed on a Biotage 75L cartridge with ethyl acetate/hexane

الإجراء التجريبي

In a 2-liter flask equipped with a septum inlet, magnetic stirring bar, and condenser leading to a mercury bubbler was placed 100 g (0.348 mol) of 4-amino-3-iodobenzotrifluoride in 1 liter DMF. To this reaction flask with stirring was added 37.4 g (0.416 mol) of copper cyanide and the contents were heated to 100° C. under nitrogen for fourteen hours. Afterwards, TLC analysis revealed minor starting material (20/80) ethyl acetate/hexane. The contents were cooled to 40° C. and filtered through a pad of Celite. The solids were washed with ether and the filtrate transferred to a separatory funnel and washed with about 5% aqueous ammonium hydroxide. The aqueous layer was back-extracted with ether and the organics were combined and washed with brine, dried over magnesium sulfate, filtered and concentrated to yield a black oil. The oil was chromatographed on a Biotage 75L cartridge with ethyl acetate/hexane to obtain 68 g 2-amino-5-(trifluoromethyl)benzonitrile as a black solid.

المصدر