[Br:1][C:2]1[CH:7]=[C:6]([CH2:8]OS(C)(=O)=O)[CH:5]=[CH:4][N:3]=1.[C-:14]#[N:15].[K+].CCOC(C)=O.C(=O)(O)[O-].[Na+]>C(O)C.O>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:14]#[N:15])[CH:5]=[CH:4][N:3]=1Methanesulfonic acid 2-bromopyridin-4-ylmethyl ester (4.24 g, 15.9 mmol) is added to a stirred solution of potassium cyanide (1.02 g, 15.1 mmol) in a mixture of ethanol (30 mL) and water (6 mL) at room temperature. After 72 hours, EtOAc (80 mL) and saturated aqueous sodium bicarbonate (40 mL) are added and the organic layer is separated. The organic layer is washed with water (3×40 mL), dried over MgSO4, filtered and concentrated. The resulting residue is purified by silica gel chromatography eluting with a gradient of 0-60% EtOAc in heptane to afford (2-bromopyridin-4-yl)-acetonitrile. MS m/z 197.4, 199.4.
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