[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5](N)=[C:4]([CH3:10])[CH:3]=1.Cl.N([O-])=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+].[Cu](C#N)[C:23]#[N:24].[C-]#N.[K+]>O>[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([C:23]#[N:24])=[C:4]([CH3:10])[CH:3]=14-Bromo-2,6dimethylaniline (4.49 g, 22.4 mmol) was taken up in water (25 ml) and concentrated hydrochloric acid (8.0 ml) was added. The mixture was sonicated to form a fine suspension and then cooled to 0° C. A solution of sodium nitrite (1.67 g, 24.2 mmol) in water (5 ml) was then added dropwise so as to maintain the temperature of the reaction between 0–5° C. The mixture was stirred at 0–5° C. for ½ h and then neutralised by addition of solid sodium carbonate. The resulting solution was then added portionwise to a solution of copper cyanide (2.42 g, 27.0 mmol) and potassium cyanide (3.65 g, 56.1 mmol) in water (25 ml) at 70° C. The mixture was stirred at 70° C. for ½ h, allowed to cool and then extracted with toluene (2 times). The combined extracts were washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica (eluant EtOAc:pet. ether 5:95) to give an orange solid; yield 3.2 g (68%).
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