Br[CH2:2][C:3]1[CH:4]=[C:5]([O:10][CH3:11])[CH:6]=[C:7]([CH3:9])[CH:8]=1.[C-]#N.[Na+].[C-]#N.C[C:18]#[N:19]>CS(C)=O>[CH3:11][O:10][C:5]1[CH:4]=[C:3]([CH2:2][C:18]#[N:19])[CH:8]=[C:7]([CH3:9])[CH:6]=1To a solution of 3-bromomethyl-5-methylanisole (17 g; 0.008 mol; from step (i) above) in DMSO (25 mL) was added NaCN (8.2 g; 0.16 mol). The mixture, which became very warm upon the addition of the cyanide, was left to cool to room temperature over 1 hour. CH3CN (25 mL) was then added, and the mixture refluxed for 1 hour. The reaction mixture was concentrated, water (200 mL) was added, and the resultant solution was extracted 3 times with ether. The combined organic phase was washed with water, dried (Na2SO4), and concentrated to give 9 g (70%) of the sub-title product as a yellow oil, which was used without further purification in the next step.
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