Sodium Cyanide → 2-(2,6-Bis(trifluoromethyl)phenyl)acetonitrile
Reaction equation
Br[CH2:2][C:3]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:6]=[CH:5][C:4]=1[C:13]([F:16])([F:15])[F:14].[C-:17]#[N:18].[Na+]>CCO.O>[F:14][C:13]([F:16])([F:15])[C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([C:9]([F:12])([F:11])[F:10])[C:3]=1[CH2:2][C:17]#[N:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 0.73 g (2.4 mmol) 2-bromomethyl-1,3-bis-trifluoromethyl-benzene and 0.183 g (3.7 mmol) sodium cyanide in 10 ml EtOH/H2O 6:1 (v/v) was hated to reflux for 3h. Then the reaction mixture was evaporated, the residue taken up in water and extracted with tert-butyl methyl ether. The combined extracts were washed with saturated aqueous NaHCO3 solution and brine, dried over Na2SO4 and evaporated. Purification by flash chromatography on silica gel with a gradient of 95:5 to 70:30% heptane/ethyl acetate provided (2,6-bis-trifluoromethyl-phenyl)-acetonitrile as colourless crystalline product of m.p. 84.5-86° C.: MS (EI): 253.0 (M.+ ), 234.1 ((M-F) .+), 233.1 ((M-HF)+.), 184.0 (((M-CF3)+.), 100%).