N,N'-Dimethylethylenediamine → alpha,alpha,alpha-Trifluoro-m-tolunitrile

Temperature

110 °C

An oven dried screw cap test tube was charged with NaCN (125 mg, 2.551 mmol), dried KI (60 mg, 0.361 mmol, 17 mol %) and CuI (40 mg, 0.210 mmol, 10 mol %), evacuated and backfilled with argon three times. 1-Bromo-3-trifluoromethylbenzene (295 μL, 2.115 mmol), N,N′-dimethylethylenediamine (225 μL, 2.110 mmol) and anhydrous toluene (1.4 mL) were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at 110 ° C. for 24 h. The resulting yellow suspension was cooled to room temperature, 2 mL of ethyl acetate, 1 mL of ammonium hydroxide (30%) and 1 mL of water were added. The mixture was stirred at 25° C. for 10 min, then the organic layer was washed with 1 mL of water and dried over MgSO4. The GC analysis showed essentially complete consumption of the starting material, and formation of the title compound (as confirmed by GC-MS).

1. customAn oven dried screw
2. customcap test tube
3. customevacuated
4. customThe tube was sealed
5. temperatureThe resulting yellow suspension was cooled to room temperature
6. stirringThe mixture was stirred at 25° C. for 10 min
7. washthe organic layer was washed with 1 mL of water
8. dry with materialdried over MgSO4
9. customconsumption of the starting material, and formation of the title compound (as confirmed by GC-MS)

ORD record

ord-cd51f910ddcc4b49b32b1479d2deef23

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07323608B2