Reaction #2329050

Reaction equation

ammonia

2-bromo-4-(trifluoromethoxy)aniline

copper cyanide

→

title compound

Yield 76.0%

2-Amino-5-trifluoromethoxybenzonitrile

Yield 76.0%

Solvents

N-methylpyrrolidone

Conditions

Workup

1. 1
   TemperatureAfter cooling to ambient temperature it
2. 2
   FiltrationThe resulting brown precipitate was collected by filtration
3. 3
   Washwashed with water (150 mL)
4. 4
   workup.DISSOLUTIONdissolved in dichloromethane (350 mL)
5. 5
   OtherThe insoluble material was removed by filtration
6. 6
   Washthe filtrate was washed with brine (100 mL)
7. 7
   Dryingdried over sodium sulfate
8. 8
   OtherPurification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 25:75:)

Procedure

To a solution of 2-bromo-4-(trifluoromethoxy)aniline (15.1 g, 60.0 mmol) in N-methylpyrrolidone (100 mL) was added copper cyanide (10.6 g, 118 mmol) and the reaction mixture was stirred for 6.5 h at 163° C. After cooling to ambient temperature it was poured onto ice-water (300 mL) and aqueous ammonia (350 mL). The resulting brown precipitate was collected by filtration, washed with water (150 mL) and dissolved in dichloromethane (350 mL). The insoluble material was removed by filtration and the filtrate was washed with brine (100 mL) and dried over sodium sulfate. Purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 25:75:) afforded the title compound (9.09 g, 76%) as a brown solid. MS: m/e=405.1 [2M+H]+.

Source