Sodium Cyanide → (4-Fluoro-2,6-dimethyl-phenyl)-acetonitrile
Reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[CH2:4]Br.[C-:12]#[N:13].[Na+]>C(O)C.O>[F:10][C:8]1[CH:9]=[C:2]([CH3:1])[C:3]([CH2:4][C:12]#[N:13])=[C:6]([CH3:11])[CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1.86 g (9 mmol) 2,6-dimethyl-4-fluoro-benzyl bromide and 0.420 g (9 mmol) sodium cyanide in 21 ml ethanol/water 6:1 was heated to reflux for 4h. The cooled reaction mixture was concentrated and extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated. Filtration of the residue through a silica gel pad with heptane/ethyl acetate 1:1 provided (4-fluoro-2,6-dimethyl-phenyl)-acetonitrile as colourless solid: MS (EI): 163.1 (M+.), 148.1 ((M-CH3)+.), 136.1 ((M-HCN)+., 100%).